- MeOTf-Induced Carboannulation of Isothiocyanates and Aryl Alkynes with C=S Bond Cleavage: Access to Indenones
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MeOTf-induced carboannulation of alkyl isothiocyanates and aryl alkynes for the synthesis of indenones in good yields under metal-free conditions with C=S bond cleavage is described. The thioalkoxy group at the 3-position of the indenone can also be converted into other functional groups, such as phenyl, methylsulfonyl, amino, and ethoxy groups.
- Zhao, Peng,Liu, Yu,Xi, Chanjuan
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- The effects of phosphine ligands on the benzannulation reaction of molybdenum carbene complexes with alkynes
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The effects of phosphine substitution at the metal on the reactions of group 6 pentacarbonyl Fischer carbene complexes with alkynes have been found not to be those expected from what is known about these reactions. The product distribution for the reaction of the molybdenum complex 5 with 3-hexyne changes dramatically from predominately indene product to predominately quinone product upon substitution of one of the CO ligands in 5a with a tri-n-butylphosphine.
- Hsung,Hsung, Richard P.,Xu,Yao-Chang, Xu,Wulff,Wulff, William D.
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- Rhodium(I)-Catalyzed Carbonylative Annulation of Iodobenzenes with Strained Olefins and 4-Octyne in the Presence of Furfural Involving ortho-C–H Bond Cleavage
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The rhodium(I)-catalyzed carbonylative annulation of iodobenzenes with strained olefins in the presence of furfural as a carbonyl source, accompanied by ortho-C–H bond cleavage, is reported. The use of 4-octyne in place of strained olefins also leads to the formation of the corresponding inden-9-one. The timely release of the carbonyl moiety via the rhodium-catalyzed decarbonylation of furfural plays a decisive role in this reaction. (Figure presented.).
- Furusawa, Takuma,Tanimoto, Hiroki,Nishiyama, Yasuhiro,Morimoto, Tsumoru,Kakiuchi, Kiyomi
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- Rapid Formation of Fluoren-9-ones via Palladium-Catalyzed External Carbon Monoxide-Free Carbonylation
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A Pd-catalyzed carbonylation reaction for the synthesis of fluoren-9-ones from 2-halogenated biphenyls using phenyl formate as a carbon monoxide surrogate was achieved. The combined use of cesium carbonate and o-anisic acid resulted in a remarkable rate e
- Konishi, Hideyuki,Futamata, Suguru,Wang, Xi,Manabe, Kei
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- Alkylations of Tetracarbonyl(phosphine)chromium and Pentacarbonylchromium Carbene Complexes and Their Reactions with Selected Acetylenes
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The thermodynamic acidity of (methylmethoxymethylene)tetracarbonyl(tri-n-butylphosphine)chromium (1b) was found to be 6 orders of magnitude less than that of (methylmethoxymethylene)pentacarbonylchromium (1a).The anion 2b is generated from 1b by deprotona
- Xu, Yao-Chang,Wulff, William D.
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- Synthesis of Indenones Via Palladium-Catalyzed Carbonylation with Mo(CO)6 as a CO Surrogate
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Transition-metal-catalyzed carbonylation of alkynes has emerged as a powerful engine for the synthesis of indenone compounds. Herein, we reported the development of an effective Pd-catalyzed ligand-free carbonylation of o-bromoaryl iodides with alkynes to afford indenone compounds. A broad range of functional groups on o-bromoaryl iodides and alkynes were tolerated in this protocol, giving carbonylation products. Furthermore, considering the factors of safety and operability, Mo(CO)6 was introduced into the reaction as a carbonyl source. Mechanistic investigations suggested that the reaction proceeded through sequential oxidative addition, alkyne insertion, carbonyl insertion, and reductive elimination steps to produce the observed carbonylation indenone products. Moreover, the indenones obtained with Mo(CO)6 as a CO surrogate can be functionalized to form synthetic useful derivatives via an environmentally friendly way.
- Li, Dong-Kun,Zhang, Bo,Ye, Qi,Deng, Wei,Xu, Zheng-Yang
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supporting information
p. 441 - 449
(2022/02/23)
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- Mechanochemical Solvent-Free Synthesis of Indenones from Aromatic Carboxylic Acids and Alkynes
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The mechanochemical solvent-free synthesis of indenones from aromatic carboxylic acids and alkynes was achieved through triflic anhydride (Tf2O)-induced cyclization reaction. A variety of indenones including a bioactive PPARγagonist were obtained in up to 90% yield at room temperature. The present protocol has the advantages of mild reaction conditions, high reaction efficiency, and feasibility of scalable synthesis, providing a facile and sustainable route to diverse indenones.
- Li, Liang,Wang, Guan-Wu
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p. 14102 - 14112
(2021/09/07)
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- Synthesis of indenones through rhodium(III)-catalyzed [3+2] annulation utilizing a recyclable carbazolyl leaving group
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The rhodium(III)-catalyzed annulative coupling of 9-ben-zoylcarbazoles with internal alkynes proceeds efficiently through ortho CH and CN bond cleavages. This reaction provides direct access to variously substituted indanone derivatives. The carbazolyl leaving group can be readily recovered and reused for preparing the starting materials.
- Ochiai, Shiho,Sakai, Asumi,Usuki, Yoshinosuke,Kang, Bubwoong,Shinada, Tetsuro,Satoh, Tetsuya
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supporting information
(2021/04/23)
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- Efficient synthesis method of 2,3-indanone
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The invention discloses an efficient synthesis method of 2,3-indanone. A heating reaction is carried out on o-substituted benzaldehyde and alkyne in an organic solvent under the catalysis of nickel and a phosphine ligand under the action of an alkali to obtain a 2,3-indanone product. O-substituted benzaldehyde and alkyne are used as raw materials, and the 2,3-indanone product is obtained in one step under the catalysis of metal nickel and the phosphine ligand under the action of the alkali, so the operation is simple and convenient, the regioselectivity is high, and the method is cheap and hasa good application prospect, and can be applied to efficient synthesis of natural products, medicines and materials.
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Paragraph 0031-0035
(2020/07/03)
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- Divergent Synthesis of α-Aroyloxy Ketones and Indenones: A Controlled Domino Radical Reaction for Di- A nd Trifunctionalization of Alkynes
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Three different modes of aldehyde/alkyne assembly through a controlled radical reaction are devised. While a double C-H activation/annulation leads to indenones, a concurrent oxidation of both aldehydes and alkynes in the course of their connection offers
- Jafarpour, Farnaz,Azizzade, Meysam,Golpazir-Sorkheh, Yekta,Navid, Hamed,Rajai-Daryasarei, Saideh
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p. 8287 - 8294
(2020/07/15)
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- Preparation method of polysubstituted indanone derivative
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The invention relates to a polysubstituted indanone derivative and a preparation method thereof, and belongs to the technical field of organic synthesis. The preparation method comprises the followingsteps: in a solvent, reacting aryl aldehyde with an alkyne derivative under an illumination condition, and carrying out post-treatment to generate the polysubstituted indanone derivative. The methodhas the advantages of simple operation, environmental friendliness, high regioselectivity, low cost, mild reaction conditions, simple operation, wide substrate range, simple post-treatment, high yield, high purity and the like.
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Paragraph 0030-0086
(2020/11/01)
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- Synthetic method of indanone and derivatives thereof
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The invention discloses a synthesis method of indanone and derivatives thereof, which comprises the following steps: adding a dialkyl acetylene compound, a palladium catalyst, an additive and an inorganic base into a dry reaction container together, and r
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Paragraph 0058-0059; 0062-0065
(2019/08/01)
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- Synthesis of Indenones via Palladium-Catalyzed Ligand-Free Carbonylation
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A palladium-catalyzed ligand-free carbonylation reaction has been developed for the synthesis of indenones. Under CO atmosphere, this cascade reaction proceeded smoothly to provide the desired indenones in moderate to excellent yields with good functional-group compatibility. The mechanistic investigations suggested the in situ formation of palladium nanoparticles and this transformation was driven by a controlled reaction sequence of alkyne insertion followed by carbonylation and annulation to form the indenone framework. (Figure presented.).
- Song, Juan,Sun, Haisen,Sun, Wei,Fan, Yuxuan,Li, Cui,Wang, Haotian,Xiao, Kang,Qian, Yan
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supporting information
p. 5521 - 5527
(2019/11/14)
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- Efficient indenones synthesis via iridium-catalyzed decarboxylative annulation between 2-oxo-2-phenylacetic acids and alkynes
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Efficient iridium-catalyzed decarboxylative annulation reactions between 2-oxo-2-phenylacetic acids and alkyne derivatives has been achieved. [IrCp*Cl2]2 with a (CH3OC6H4)3P ligand, AgSbF6 and Cu(OAc)2 additives was the most efficient catalytic system for this transformation. This reaction is suitable for a broad range of alkynes and 2-oxo-2-phenylacetic acids and a variety of indenone derivatives were obtained in medium to high yields. This work provides an efficient approach for the construction of indenones by iridium–catalyzed decarboxylative annulation.
- Yu, Xiaobo,Geng, Shudong,Liu, Guanchen,Guo, Weijie,Wang, Jianhui
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p. 139 - 143
(2018/11/23)
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- Synthesis method for 2,3-diphenyl-1H-indene-1-one derivatives
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The invention discloses a synthesis method for 2,3-diphenyl-1H-indene-1-one derivatives. The synthesis method comprises the steps of: adding benzoyl formic acid, a diphenyl acetylene compound, pentamethyl cyclopentadiene dichloride iridium, copper acetate, silver hexafluoroantimonate and a silver hexafluoroantimonate into an organic solvent; heating for reaction in the presence of air; and after the reaction, carrying out post-treatment to obtain the 2,3-diphenyl-1H-indene-1-one derivative. The method synthesizes the 2,3-diphenyl-1H-indene-1-one derivative in one step through simple and easilyavailable raw materials, so that the conversion efficiency is high and the atomic economical benefit is good. Meanwhile, the synthetic method is simple to operate, high in reaction yield and wide inprimer adaptability.
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Paragraph 0028; 0029; 0030; 0031; 0032; 0033; 0038
(2019/01/21)
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- Ferrocene-Initiated Oxidative Cyclization of Benzaldehyde with Alkyne: New Strategy to Substituted Indenones
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A ferrocene-initiated oxidative cyclization of benzaldehyde with alkyne was successfully developed as a novel strategy for direct access to substituted indenones in high yields. The commercially available and cheap ferrocene was employed as an initiator. This transformation could proceed smoothly with a low initiator loading (0.5 mol-%) and provide the titled products up to 90 % yield with atom-, step-economy and good substrates tolerance. The indenones obtained would be important building blocks in organic synthesis.
- Feng, Yadong,Zhang, Hong,Yu, Yunliang,Yang, Lei,Cui, Xiuling
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supporting information
p. 2740 - 2744
(2019/04/17)
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- A polysubstituted indenone derivatives and its preparation method (by machine translation)
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The present invention discloses a multi-substituted indenone derivatives and its preparation method, its structural formula is: Wherein R1 Is alkyl, halogen, methoxy, trifluoromethyl, N, N - dimethyl or methylthio, R2 is aryl. Synthesis of this invention has a plurality of substituted base yinyin alkone derivatives, from the point of view of pharmaceutical chemistry has far-reaching significance. The method of this invention easily obtained raw material, economic low-cost, high yield, mild reaction conditions, wide substrate range, easy post treatment. (by machine translation)
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Paragraph 0022-0039
(2019/04/17)
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- Palladium(ii)-catalyzed synthesis of indenones through the cyclization of benzenecarbaldehydes with internal alkynes
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The palladium(ii)-catalyzed carbocyclization of benzenecarbaldehydes with internal alkynes to afford 2,3-disubstituted indenones was reported. The annulation reaction proceeded through the transmetalation of Pd(ii) with an aromatic aldehyde and the insertion of internal alkynes, followed by cyclization via the intramolecular nucleophilic addition of intermediate organopalladium(ii) species to the aldehyde group. This reaction proceeded in moderate to good yields with high regioselectivity.
- Kashanna, Jajula,Aravind Kumar, Rathod,Kishore, Ravada
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p. 31162 - 31168
(2019/10/28)
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- Palladium-Catalyzed Benzofulvenation of o-Arylanilines through C?H Bond Activation by Using Two Diarylacetylenes as an Implicit Benzofulvene
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We report the first example of Pd(II)-catalyzed highly step- and atom-economical benzofulvenation through free amine-directed ortho C?H bond activation of o-arylanilines. This paper presents a novel, simple, and efficient approach for the synthesis of benzofulvene derivatives from o-arylaniline substrates through C?H bond activation with two diarylacetylenes as an implicit benzofulvene unit. The reactivity of synthesized benzofulvenes toward oxidation was investigated, and they were shown to transform into phenanthridines, oxabenzofulvenes, and fluorescent polycyclics. (Figure presented.).
- Raju, Selvam,Hsiao, Huan-Chang,Thirupathi, Selvakumar,Chen, Pei-Ling,Chuang, Shih-Ching
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supporting information
p. 683 - 689
(2019/01/04)
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- Nickel-Catalyzed Arylative Carboxylation of Alkynes with Arylmagnesium Reagents and Carbon Dioxide Leading to Trisubstituted Acrylic Acids
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Nickel-catalyzed arylcarboxylation of alkynes with arylmagnesium reagents and carbon dioxide (CO2, 1 atm) was realized in one pot. Various trisubstituted acrylic acids within an aryl group at the β-position have been prepared efficiently with good regioselectivity under mild conditions. The resulting products could be further transformed to benzoannelated cycles retaining CO2 as a one-carbon synthon.
- Wang, Sheng,Xi, Chanjuan
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p. 4131 - 4134
(2018/07/15)
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- An Approach to One-Pot Regioselective Synthesis of Indenones through Palladium-Catalyzed Annulation in Water
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A one-pot synthesis of indenones is presented. The process involves palladium-catalyzed annulation of ortho-halobenzaldehydes with internal alkynes. Notably, it proceeded successfully in water as the sole, and green, solvent. Significantly, unlike in earlier reports, this protocol showed excellent regioselectivity with unsymmetrical alkylarylacetylenes. Further, the strategy was extended to a one-pot synthesis of a neolignan natural product.
- Ramesh, Karu,Satyanarayana, Gedu
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p. 4135 - 4146
(2018/08/11)
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- The Synthesis of Benzofulvenes through Palladium-Catalyzed Sequential Three-Component Reactions
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An approach for the synthesis of benzofulvenes has been developed through palladium-catalyzed sequential three-component reactions. The reactions likely involve C,C-palladacycles as the key intermediates. The palladacycles are generated through cascade reactions of aryl halides and alkynes, and then reacted with CH2Br2 to form benzofulvenes as the final products. (Figure presented.).
- Zhou, Bo,Wu, Zhuo,Qi, Weixin,Sun, Xueliang,Zhang, Yanghui
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supporting information
p. 4480 - 4484
(2018/10/31)
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- Rhodium-catalyzed carbonylative annulation of 2-bromobenzylic alcohols with internal alkynes using furfural via β-aryl elimination
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In spite of the significant progress made in transformations of unstrained benzylic (tert-)alcohols through β-aryl elimination, catalytic carbonylation has not yet been developed extensively because alkoxycarbonylation is probably favored over β-aryl elim
- Furusawa, Takuma,Tanimoto, Hiroki,Nishiyama, Yasuhiro,Morimoto, Tsumoru,Kakiuchi, Kiyomi
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supporting information
p. 926 - 929
(2017/06/27)
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- Iodine-Mediated Cyclization of ortho-Alkynylaryl Ketones for the Synthesis of Indenone Derivatives
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A new method for the synthesis of indenone derivatives based on the I2-promoted cyclization of ortho-alkynylaryl ketones has been developed. This method provides a metal-free and convenient route for the regioselective synthesis of indenones using ortho-alkynylaryl ketones with predefined substituents to give indenone products in moderate to good yields.
- Chuangsoongnern, Pennapa,Surinrach, Chareef,Tummatorn, Jumreang,Thongsornkleeb, Charnsak,Ruchirawat, Somsak
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p. 5102 - 5109
(2017/09/23)
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- Water-assisted metal-free catalyzed cyclization of 2-alkynylarylketones: A facile approach to indenones
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A simple and directed synthetic strategy starting from 2-alkynylarylketones was developed for the construction of various indenones under metal-free and water-assisted conditions. This intramolecular cyclization reaction could well tolerate a wide range of functional groups, and the corresponding functionalized indenones were obtained in moderate to excellent yields (up to 94%). In addition, the possible mechanism of this reaction may involve isobenzofuranium intermediates.
- Zhang, Shuai,Bai, Xue-Ting,Chen, Dan-Yun,Chen, Pei,Zhang, Qian-Qian,Wang, Yan-Bo
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p. 31142 - 31147
(2017/07/11)
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- Rhodium-Catalyzed Oxidative Decarboxylation Annulation Reactions of Mandelic Acids and Alkynes: An Efficient Synthetic Method for Indenones
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Efficient rhodium-catalyzed oxidative decarboxylation annulation reactions between mandelic acids and alkyne derivatives are described. The desired indenone products were obtained in medium to good yields under the optimized reaction conditions, which were a [RhCp*Cl2]2 catalyst (10.0 mol %) in combination with a PCy3 ligand (10.0 mol %) and AgSbF6 (10 mol %) and Cu(OAc)2 (20 mol %) additives. Many functional groups are compatible with the reaction under the optimized reaction conditions. This strategy provides a promising method for the construction of indenones from cheap and commercially available starting materials.
- Yu, Xiaobo,Duan, Yulian,Guo, Weijie,Wang, Tao,Xie, Qingxiao,Wu, Shutao,Jiang, Chenggong,Fan, Zixiong,Wang, Jianhui,Liu, Guiyan
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p. 1027 - 1034
(2017/04/21)
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- Cobalt(III)-catalyzed annulation of esters and alkynes: A facile route to indenones
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An efficient protocol for the synthesis of indenones has been developed via the annulation of benzoic esters and internal alkynes by exploiting the cobalt catalyst.
- Yu, Wenlong,Zhang, Wei,Liu, Zhanxiang,Zhang, Yuhong
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supporting information
p. 6837 - 6840
(2016/06/01)
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- Palladium(II)-Catalyzed Annulation of Alkynes with 2-(Cyanomethyl)phenylboronates Leading to 3,4-Disubstituted 2-Naphthalenamines
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1,2-Bis(diphenylphosphino)ethane (dppe)-ligated palladium(II) complexes catalyze the annulation of internal alkynes with 2-(cyanomethyl)phenylboronates to provide 3,4-disubstituted-2-naphthalenamines in good yields. The annulation reaction proceeds under mild and neutral conditions and requires methanol as an essential solvent. In addition to symmetrical alkynes, unsymmetrical alkynes substituted by aryl, alkyl, and alkynyl groups participate in the annulation to afford the corresponding 2-naphthalenamines with electron-withdrawing sp2- and sp-carbons preferentially located at the C-3 position. Substituents including an alkyl or alkoxy group on the cyanomethyl moiety and a halogen atom on the benzene ring in the boronates are compatible with the reaction conditions. The annulation proceeds through the transmetalation of the palladium(II) complexes with the boronates and alkyne insertion followed by nucleophilic addition of the generated alkenylpalladium(II) species to the intramolecular cyano group. Stoichiometric reactions revealed that the methanol solvent was effective for both transmetalation and catalyst regeneration.
- Tsukamoto, Hirokazu,Ikeda, Taishi,Doi, Takayuki
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p. 1733 - 1745
(2016/03/15)
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- Synthesis of 2,3-disubstituted indenones by cobalt-catalyzed [3+2] annulation of: O -methoxycarbonylphenylboronic acid with alkynes
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Treatment of alkynes with o-methoxycarbonylphenylboronic acid in the presence of a cobalt catalyst resulted in the corresponding 2,3-disubstituted indenones in good yields. Excellent regioselectivities were observed, when silyl aryl alkynes were used. The intermediate 3-silyl-2-aryl-substituted indenones were converted to 2,3-diaryl indenones by a three-step protocol involving C-Si bromination and Suzuki-Miyaura coupling reaction.
- Ueda, Mitsuhiro,Ueno, Tamami,Suyama, Yuki,Ryu, Ilhyong
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supporting information
p. 13237 - 13240
(2016/11/17)
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- Pd(0)-catalyzed CO gas-free carbonylation of 2-bromobiphenyls with formaldehyde as a carbonyl surrogate through the cleavage of a CH bond
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Paraformaldehyde serves as a carbonyl source in the Pdcatalyzed cyclocarbonylation of 2-bromobiphenyls through the cleavage of a CH bond to afford good yields of fluoren-9-one derivatives. This protocol is also applicable to the reaction of β-bromostyrene, leading to the construction of an indenone framework.
- Furusawa, Takuma,Morimoto, Tsumoru,Oka, Nagato,Tanimoto, Hiroki,Nishiyama, Yasuhiro,Kakiuchi, Kiyomi
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supporting information
p. 406 - 408
(2016/05/09)
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- Gold-Catalyzed Ammonium Acetate Assisted Cascade Cyclization of 2-Alkynylarylketones
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An ammonium acetate assisted gold-catalyzed cascade cyclization reaction of 2-alkynylarylketones is described. Under the reported conditions, a gold-catalyzed intramolecular cyclization of 2-alkynylarylketones takes place through two competing reaction mechanisms?-?a 5-exo-dig or a 6-endo-dig cyclization-leading to two regioisomeric intermediates: isobenzofuranium or isobenzopyrylium. In the presence of ammonium acetate, the two intermediate compounds undergo further rearrangement to 2,3-disubstituted indenones and 1,3-disubstituted isoquinolines, respectively. While both reaction pathways proceed via a cyclization-rearrangement cascade, the gold-mediated 5-exo-dig process is especially notable, as it provides a novel cyclization protocol of 2-alkynylarylketones.
- Domaradzki, MacIej E.,Long, Yuhua,She, Zhigang,Liu, Xiaochen,Zhang, Gan,Chen, Yu
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p. 11360 - 11368
(2015/12/01)
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- Rhodium-catalyzed direct coupling of benzothioamides with alkenes and alkynes through directed C-H bond cleavage
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Rhodium-catalyzed direct coupling of benzothioamides with alkenes proceeds smoothly involving ortho-CH bond cleavage. The thioamides also couple with alkynes under similar conditions accompanied by desulfurization and CN bond cleavage to produce indenone derivatives.
- Yokoyama, Yuki,Unoh, Yuto,Bohmann, Rebekka Anna,Satoh, Tetsuya,Hirano, Koji,Bolm, Carsten,Miura, Masahiro
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p. 1104 - 1106
(2015/09/02)
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- Ruthenium(II)-catalyzed C-H bond activation: An efficient route toward indenamines
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An efficient and atom-economical method for the synthesis of substituted indenamines from N-tosylarylimines and alkynes via ruthenium(II)-catalyzed C-H bond activation and annulation is described. The catalytic reaction proceeds well with a broad substrate scope and in good yields. A possible mechanism is proposed that involves imine nitrogen chelation-assisted ortho-C-H bond activation of the substrate, alkyne insertion, and intramolecular insertion of the C£ NTs group into the C-Ru bond. Isotope-labeling experiments are performed to understand the underlying mechanism of the reaction. Atomic bean counters succeed! An efficient and atom-economical method for the synthesis of substituted indenamines from N-tosylarylimines and alkynes via ruthenium(II)-catalyzed C-H bond activation and annulation is described.
- Hung, Chen-Hsun,Gandeepan, Parthasarathy,Cheng, Chien-Hong
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p. 2692 - 2697
(2015/04/14)
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- MeOTf-induced carboannulation of arylnitriles and aromatic alkynes: A new metal-free strategy to construct indenones
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MeOTf-induced carboannulation of arylnitriles and aromatic alkynes for synthesis of indenones under metal-free conditions has been described. When ortho-substituted benzonitriles were used, indeno[1,2-c]isoquinolines were formed.
- Yan, Xiaoyu,Zou, Song,Zhao, Peng,Xi, Chanjuan
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supporting information
p. 2775 - 2777
(2014/03/21)
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- Palladium-catalyzed annulation of internal alkynes in aqueous medium
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To facilitate precatalyst recovery and reuse, we have developed a fluorous, oxime-based palladacycle 1 and demonstrated that it is a very efficient and versatile precatalyst for carbo- and heteroannulation of internal alkynes with functionalized aryl halides in aqueous medium. A uniform reaction condition for these annulation reactions was also developed.
- Ang, Wei Jie,Tai, Chih-Hsuan,Lo, Lee-Chiang,Lam, Yulin
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p. 4921 - 4929
(2014/01/23)
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- Palladium-catalyzed annulation of alkynes with ortho -halide-containing benzyl alcohols in aqueous medium
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The Pd-catalyzed annulations of ortho-halide-containing benzyl alcohols with alkynes for the synthesis of indenones were achieved in aqueous Triton X-100 micelles with good yields and wide substrate scopes. Moreover, the indenones obtained in this procedure can be further functionalized to form some more synthetic useful derivatives via an environmental-friendly way.
- Feng, Jie,Lu, Guoping,Lv, Meifang,Cai, Chun
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p. 10561 - 10567
(2015/02/19)
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- Access to indenones by rhodium(III)-catalyzed C-H annulation of arylnitrones with internal alkynes
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Under redox-neutral conditions, rhodium(III)-catalyzed C-H annulation of N-tert-butyl-α-arylnitrones with internal alkynes has been realized for the synthesis of indenones under mild conditions. This reaction proceeded in moderate to high yields and with
- Qi, Zisong,Wang, Mei,Li, Xingwei
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supporting information
p. 5440 - 5443
(2013/11/19)
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- Rhodium(III)-catalyzed annulation of azomethine ylides with alkynes via C-H activation
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The rhodium(III)-catalyzed coupling of azomethine ylides with alkynes via C-H activation has been developed for the synthesis of indenamines in moderate to high yields. The coupled products can be further oxidized to indenones and derivatives.
- Chen, Yuye,Wang, Fen,Zhen, Wencui,Li, Xingwei
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supporting information
p. 353 - 359
(2013/05/08)
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- Rhodium-catalyzed direct annulation of aldehydes with alkynes leading to indenones: Proceeding through in situ directing group formation and removal
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The Rh-catalyzed direct annulation of an aldehyde with an alkyne leading to indenone was achieved. The in situ temporal installation of acetylhydrazine enables the annulation of the ortho arene C-H bond with alkynes to form ketone hydrazone. Subsequently, the in situ directing group removal takes place since ketone hydrazone is more susceptible toward hydrolysis than aldehyde hydrazone. Notably, this procedure tolerates a series of functional groups, such as methoxyl, acetylamino, fluoro, trifluoromethyl, methoxycarbonyl, chloro, and bromo groups.
- Chen, Shuyou,Yu, Jintao,Jiang, Yan,Chen, Fan,Cheng, Jiang
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supporting information
p. 4754 - 4757
(2013/10/08)
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- Ruthenium- and sulfonamide-catalyzed cyclization between N-sulfonyl imines and alkynes
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Ruthenium(II)-catalyzed redox-neutral annulative coupling of N-sulfonyl imines with alkynes has been achieved for the synthesis of indenamines, where a sulfonamide cocatalyst is necessary.
- Zhao, Peng,Wang, Fen,Han, Keli,Li, Xingwei
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p. 5506 - 5509,4
(2020/10/15)
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- Molecular iodine mediated cyclization reactions of 2-(1-alkynyl)benzylic alcohols to substituted indenones
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An efficient I2-mediated approach to the synthesis of disubstituted indenones from readily available 2-alkynylbenzyl alcohols in the presence of H2O has been developed. These results are different from the known iodocyclization react
- Wang, Chengyu,Yang, Jingyu,Cheng, Xingcan,Li, Ende,Li, Yanzhong
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supporting information; experimental part
p. 4402 - 4404
(2012/09/25)
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- Photochemical studies on aromatic γ,δ-epoxy ketones: Efficient synthesis of benzocyclobutanones and indanones
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Irradiation of terminal aromatic γ,δ-epoxy ketones with a 450 W UV lamp led to Norrish type II cyclization/semi-pinacol rearrangement cascade reaction which formed the benzocyclobutanones containing a full-carbon quaternary center, whereas irradiation of substituted aromatic γ,δ-epoxy ketones led to the indanones through a photochemical epoxy rearrangement and 1,5-biradicals cyclization tandem reaction.
- Shao, Yutian,Yang, Chao,Gui, Weijun,Liu, Yang,Xia, Wujiong
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p. 3560 - 3562
(2012/06/04)
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- Rhodium/copper-catalyzed annulation of benzimides with internal alkynes: Indenone synthesis through sequential C-H and C-N cleavage
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Doubled up: A rhodium(III)/copper(II) system co-catalyzes the annulation of benzimides with internal alkynes for the synthesis of indenones (see scheme; Cp=C5Me5). The reaction involves an uncommon nucleophilic addition of a transition-metal-carbon bond to an imide moiety. This novel reaction provides a facile route to synthesize indenones from readily available benzimides and internal alkynes. Copyright
- Li, Bi-Jie,Wang, Hao-Yuan,Zhu, Qi-Lei,Shi, Zhang-Jie
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p. 3948 - 3952
(2012/05/20)
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- Regioselective arylation and alkynylation of 2,3-dibromo-1h-inden-1-one by Suzukii-Miyaura and Sonogashira cross-coupling reactions
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Suzukii-Miyaura reactions of 2,3-dibromo-1H-inden-1-one afforded a wide range of arylated 1H-inden-1-ones. Sonogashira cross-coupling reactions gave alkynylated indenones. The reactions proceeded with very good regioselectivity in the less sterically hind
- Khera, Rasheed Ahmad,Hussain, Munawar,Hung, Nguyen Thai,Eleya, Nadi,Feist, Holger,Villinger, Alexander,Langer, Peter
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experimental part
p. 469 - 482
(2012/05/04)
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- Facile synthesis of indenones by cyclopalladated ferrocenylimine-catalyzed annulation of internal alkynes
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An efficient and facile protocol for the annulation of o-halobenzaldehyde derivatives with diverse internal alkynes has been developed using cyclopalladated ferrocenylimine as the catalyst, and the indenones as the products could be obtained in moderate t
- Zhang, Junli,Yang, Fan,Wu, Yangjie
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experimental part
p. 675 - 679
(2012/01/05)
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- An indenone synthesis involving a new aminotransfer reaction and its application to dibenzopentalene synthesis
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o-(Phenylethynyl)phenyllithiums, generated by treatment of o-(phenylethynyl)bromobenzenes with tBuLi, were quenched with N,N-dimethylcarboamides to afford various 2-phenylindenone derivatives in moderate to good yields upon acidic workup. The choice of lithiation reagents was critical. When n-butyllithium was used the yields were reduced. The N-alkyl groups in the carboamides were also important: quenching with N,N-diethylbenzamides also afforded 2,3-diphenylindenones as the sole isolated products, but quenching with N-benzoylpiperidine led to 2-benzoyltolane in good yield. Control experiments revealed that the reactions proceed through a multi-step reaction sequence involving a novel intramolecular transamination to the α-acetylenic carbon of the alkynyl group. The method was applicable to the synthesis of dibenzopentalene derivatives as well as various indenone derivatives. A mechanism for the reaction is discussed.
- Katsumoto, Kenta,Kitamura, Chitoshi,Kawase, Takeshi
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scheme or table
p. 4885 - 4891
(2011/10/31)
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- Facile synthesis of isoquinolines by imination and subsequent palladacycle-catalyzed iminoannulation of internal alkynes
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An efficient and facile synthesis of isoquinolines has been described via a tandem reaction of imination of o-halobenzaldehydes with tert-butyl amine and subsequent palladacycle-catalyzed iminoannulation of internal alkynes. This tandem reaction could be carried out successively in one pot without any special operation, and the annulation step could afford isoquinolines derivatives in moderate to good yields with high regioselectivity. In addition, the simple synthesis of indoles was realized by palladacycle-catalyzed annulation of o-iodoaniline or o-bromoanilines with internal alkynes.
- Yang, Fan,Zhang, Junli,Wu, Yangjie
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experimental part
p. 2969 - 2973
(2011/05/02)
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- Site-selective Suzuki-Miyaura reactions of 2,3-dibromo-1H-inden-1-one
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The first transition metal-catalyzed cross-coupling reactions of 2,3-dibromo-1H-inden-1-one are reported. The Suzuki-Miyaura reaction of 2,3-dibromo-1H-inden-1-one with 2 equiv of arylboronic acid gave 2,3-diaryl-1H-inden-1-ones. The reaction with 1 equiv of arylboronic acid gave 2-bromo-3-aryl-1H-inden-1-ones with very good site-selectivity. The one-pot reaction of 2,3-dibromo-1H-inden-1-one with two different arylboronic acids afforded 2,3-diaryl-1H-inden-1-ones containing two different terminal aryl groups.
- Hussain, Munawar,Hung, Nguyen Thai,Khera, Rasheed Ahmed,Villinger, Alexander,Langer, Peter
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experimental part
p. 184 - 187
(2011/02/26)
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- Rhenium-catalyzed synthesis of indenones by novel dehydrative trimerization of aryl aldehydes via C-H bond activation
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By heating aryl aldehydes with catalytic amounts of a rhenium complex, ReBr(CO)5, and N-phenylacetamide in toluene, indenone derivatives are obtained in good to excellent yields. This reaction proceeds via (1) the formation of an isobenzofuran derivative by the insertion of an aldehyde into the C-H bond of another aldehyde (C-H bond activation) and successive intramolecular nucleophilic cyclization, (2) nucleophilic addition of the formed isobenzofuran derivative to the third aldehyde, (3) isomerization, and (4) intramolecular aldol condensation.
- Kuninobu, Yoichiro,Matsuki, Takashi,Takai, Kazuhiko
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scheme or table
p. 2948 - 2950
(2010/09/10)
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- Rhodium catalyzed reaction of internal alkynes with organoborons under CO atmosphere: a product tunable reaction
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Alkynes react with organoborons under a CO atmosphere in the presence of a rhodium(I) catalyst to afford mainly 5-aryl-2(5H)-furanones, α,β-unsaturated ketones, and indanones. The product selectivity can be tuned by modifying the reaction conditions.
- Artok, Levent,Ku?, Melih,Aksin-Artok, ?zge,Dege, Fatma Nurcan,?zkilin?, Fatma Yelda
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experimental part
p. 9125 - 9133
(2010/01/16)
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- Rh(l)-catalyzed CO gas-free carbonylative cyclization reactions of alkynes with 2-bromophenylboronic acids using formaldehyde
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The rhodium(l)-catalyzed reaction of alkynes with 2-bromophenylboronic acids in the presence of paraformaldehyde resulted in a CO gas-free carbonylative cyclization, yielding indenone derivatives. [RhCI(BINAP)] 2 and [RhCI(cod)]2 wer
- Morimoto, Tsumoru,Yamasaki, Kae,Hirano, Akihisa,Tsutsumi, Ken,Kagawa, Natsuko,Kakiuchi, Kiyomi,Harada, Yasuyuki,Fukumoto, Yoshiya,Chatani, Naoto,Nishioka, Takanori
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supporting information; experimental part
p. 1776 - 1780
(2009/09/08)
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- Cobalt-catalyzed regioselective synthesis of indenamine from o-lodobenzaldimine and alkyne: Intriguing difference to the nickel-catalyzed reaction
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A new and convenient method for the regioselective synthesis of indenamine from the corresponding o-halobenzyaldehyde, amine, and alkyne in the presence of zinc powder catalyzed by cobalt complexes, was reported. The indenamines and indene-enamine gave the corresponding imine derivatives upon treatment with TBAF in THF at 40°C. The results show that chelation-assisted oxidative addition of 2-iodo-benzaldinine to CobaltI, which is formed from the reduction of CoIII by zinc, gives a five-membered ring cobaltacycle. The nickel-catalyzed reaction and reductive elimination takes place to afford an isoquinolinium salt and then the isoquinoline product. The regiochemistry for the cobalt-catalyzed indenamine and nickel-catalyzed isoquinoline formation is opposite to each other when alkynes with an electron-withdrawing group are used.
- Liu, Chuan-Che,Korivi, Rajendra Prasad,Cheng, Chien-Hong
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supporting information; experimental part
p. 9503 - 9506
(2009/10/02)
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