- Palladium-Catalyzed Synthesis of Dihydrobenzoindolones via C-H Bond Activation and Alkyne Insertion
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A palladium-catalyzed intramolecular carbopalladation, intramolecular C-H bond activation, and alkyne insertion sequence for the generation of dihydrobenzoindolones is described. Products are obtained in moderate to excellent yields as single regioisomers
- Rodríguez, José F.,Marchese, Austin D.,Lautens, Mark
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- Synthesis and cytotoxic activity of novel hexahydropyrrolo[2,3-b]indole imidazolium salts
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A series of novel hexahydropyrrolo[2,3-b]indole-1H-imidazolium salts were synthesized and evaluated in vitro against a panel of human tumor cell lines. The results suggest that the 5,6-dimethyl-benzimidazole ring, and substitution of the imidazolyl-3-posi
- Zhou, Yunjing,Duan, Kunyun,Zhu, Liang,Liu, Zhengfeng,Zhang, Chaobo,Yang, Lijuan,Li, Minyan,Zhang, Hongbin,Yang, Xiaodong
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- Palladium-Catalyzed Enantioselective Intramolecular Heck Carbonylation Reactions: Asymmetric Synthesis of 2-Oxindole Ynones and Carboxylic Acids
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Herein, we report a Pd-catalyzed enantioselective domino Heck carbonylation reaction of o-iodoacrylanilides with terminal alkynes and water as the nucleophiles, affording a diversity of β-carbonylated 2-oxindole derivatives bearing a 3,3-disubstituted all-carbon quaternary stereocenter, in high yields (55–99 %) with good to excellent enantioselectivities (up to 99 % ee). The synthetic utilities of the protocol were demonstrated in the gram-scale synthesis of 2-oxindole-derived ynone 3 ea and carboxylic acid 4 a, as well as the facile synthesis of chiral 2-oxindoles with a pyrazole or isoxazole moiety.
- Zhang, Di,Xiong, Youyuan,Guo, Yingjie,Zhang, Lei,Wang, Zheng,Ding, Kuiling
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(2021/10/25)
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- Palladium-Catalyzed Domino Heck/Sulfination: Synthesis of Sulfonylated Hetero- And Carbocyclic Scaffolds Using DABCO-Bis(sulfur dioxide)
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The synthesis of a broad variety of hetero- and carbocyclic scaffolds via a Pd-catalyzed domino Heck/SO2 insertion reaction is reported. This reaction utilizes DABSO, a safe and easy-to-handle alternative to SO2 gas. The reaction proceeds through a sulfin
- Bajohr, Jonathan,Diallo, Abdoul G.,Whyte, Andrew,Gaillard, Sylvain,Renaud, Jean-Luc,Lautens, Mark
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p. 2797 - 2801
(2021/04/13)
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- Palladium-Catalyzed Domino Synthesis of 2,3-Difunctionalized Indoles via Migratory Insertion of Isocyanides in Batch and Continuous Flow
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We report, herein, a palladium-catalyzed cascade comprising carbopalladation, migratory insertion of isocyanide and triple bond activation followed by a nucleophilic attack (OR?) to construct difunctionalized acyl indoles. The process involves
- Chen, Su,Oliva, Monica,Van Meervelt, Luc,Van der Eycken, Erik V.,Sharma, Upendra K.
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p. 3220 - 3226
(2021/06/01)
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- Nickel-Catalyzed Arylcarbamoylation of Alkenes of N-(o-Iodoaryl)acrylamides with Nitroarenes via Reductive Aminocarbonylation: Facile Synthesis of Carbamoyl-Substituted Oxindoles
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Nickel-catalyzed arylcarbamoylation reactions of alkenes of N-(o-haloaryl)acrylamides with CO and nitroarenes via reductive aminocarbonylation to produce carbamoyl-substituted oxindoles with an all-carbon quaternary stereogenic center are presented. Starting with N-(o-haloaryl)acrylamides, simple CO, and inexpensive nitroarenes and using a Ni catalyst, a dinitrogen-based ligand, a Zn reductant, a TMSCl additive, and a base system, this protocol enables the synthesis of various carbamoyl-substituted oxindoles and allows the efficient late-stage derivatization of valuable molecules.
- Cheng, Chaozhihui,Xiang, Jian-Nan,Zhu, Yan-Ping,Peng, Zhi-Hong,Li, Jin-Heng
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p. 9543 - 9547
(2021/12/14)
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- Pd/Cu-Catalyzed Enantioselective Sequential Heck/Sonogashira Coupling: Asymmetric Synthesis of Oxindoles Containing Trifluoromethylated Quaternary Stereogenic Centers
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An asymmetric palladium and copper co-catalyzed Heck/Sonogashira reaction between o-iodoacrylanilides and terminal alkynes to synthesize chiral oxindoles was developed. In particular, a wide range of CF3-substituted o-iodoacrylanilides reacted
- Bai, Xingfeng,Wu, Caizhi,Ge, Shaozhong,Lu, Yixin
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supporting information
p. 2764 - 2768
(2019/12/24)
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- 3,3′-Disubstituted Oxindoles Formation via Copper-Catalyzed Arylboration and Arylsilylation of Alkenes
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Arylboration and arylsilylation reactions of N-(2-iodoaryl)acrylamides with bis(pinacolato)-diboron (B2pin2) or PhMe2Si-Bpin are developed by using simple CuOAc as the sole catalyst. A range of boron-or silane-bearing 3,3′-disubstituted oxindoles are obtained in moderate to excellent yields. The reaction is proposed to proceed via a domino sequence involving intermolecular olefin borylcupration or silylcupration followed by intramolecular coupling of an alkyl-Cu intermediate with aryl iodide.
- Liang, Ren-Xiao,Chen, Ru-Yi,Zhong, Chao,Zhu, Jia-Wen,Cao, Zhong-Yan,Jia, Yi-Xia
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p. 3215 - 3218
(2020/04/10)
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- Nickel-catalyzed reductive aryl thiocarbonylation of alkene via thioester group transfer strategy
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Herein reported is a nickel-catalyzed reductive aryl thiocarbonylation of alkene via thioester group transfer strategy by using simple and readily available thioesters. In contrast to traditional activation of weaker C(acyl)-S bond, the C(acyl)-C bond of
- Feng, Yunxia,Yang, Shimin,Zhao, Shen,Zhang, Dao-Peng,Li, Xinjin,Liu, Hui,Dong, Yunhui,Sun, Feng-Gang
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supporting information
p. 6734 - 6738
(2020/09/15)
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- Synthesis of oxindoles via Cu-mediated reactions between N-phenylacrylamides and ethyl 2-bromo-2-methylpropionate
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A novel way of synthesizing alkylated oxindoles via Cu-mediated atom transfer radical addition reaction between N-phenylacrylamides and ethyl 2-bromo-2-methylpropionate has been described. It was found that the use of N,N,N′,N′-1,1,2,2,-tetramethylethylenediamine as ligand was important for achieving good yields. Additionally, the use of DMSO as solvent and running the reaction at 130 °C were also crucial. In some cases, the product can be further brominated when the reaction temperature was raised to 150 °C.
- Liu, Da,Zhuang, Shaobo,Chen, Xiang,Yu, Lin,Yu, Yongqi,Hu, Liang,Tan, Ze
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supporting information
p. 612 - 616
(2018/01/18)
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- Nickel-Catalyzed Domino Heck Cyclization/Suzuki Coupling for the Synthesis of 3,3-Disubstituted Oxindoles
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The first nickel-catalyzed domino Heck cyclization/Suzuki coupling reaction for the synthesis of 3,3-disubstituted oxindoles bearing quaternary all-carbon centers is reported. A wide range of electrophiles, such as aryl iodides, bromides, triflates, and c
- Li, Yuxiu,Wang, Kuai,Ping, Yuanyuan,Wang, Yifan,Kong, Wangqing
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p. 921 - 924
(2018/02/22)
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- Palladium-Catalyzed Domino Heck/Silylation Reaction for the Synthesis of (2-Oxoindolin-3-yl)methylsilanes via Trapping of the σ-Alkylpalladium Intermediates with Disilanes
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A palladium-catalyzed domino Heck/silylation reaction of acrylamides with hexamethyldisilane is presented. This transformation, which involves the formation of a σ-alkylpalladium intermediate, allows direct access to functionalized (2-oxoindolin-3-yl)methylsilanes in good to excellent yields. Furthermore, this strategy could be utilized for the synthesis of (2-oxoindolin-3-yl)methylstannanes from hexamethyldistannane. (Figure presented.).
- Xiao, Genhua,Chen, Liang,Zhou, Bang,Deng, Guobo,Gong, Jun,Liang, Yun
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p. 3477 - 3481
(2018/09/14)
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- Catalytic Enantioselective Double Carbopalladation/C?H Functionalization with Statistical Amplification of Product Enantiopurity: A Convertible Linker Approach
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Combining a catalytic enantioselective reaction with dimerization in a single operation is an efficient way to upgrade the enantiomeric excesses (ee) of the product. Palladium-catalyzed reaction of N-(2-iodophenyl)-N-methyl methacrylamide derivatives with
- Tong, Shuo,Limouni, Aurore,Wang, Qian,Wang, Mei-Xiang,Zhu, Jieping
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supporting information
p. 14192 - 14196
(2017/10/31)
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- Silver-Catalyzed Decarboxylative Radical Addition/Cyclization of α,α-Difluoroarylacetic Acids with Acrylamides To Synthesize Difluorinated Oxindoles
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A facile silver-catalyzed decarboxylative radical addition/cyclization reaction of α,α-difluoroarylacetic acids and acrylamides has been disclosed. The method provides a highly attractive approach to synthesize a series of difluorinated oxindoles that contain various functional groups in moderate to good yields under mild conditions. Moreover, experimental studies reveal that the CF2 group of the α,α-difluoroarylacetic acids plays a vital role in the transformation.
- Li, Yin-Long,Wang, Ji-Bo,Wang, Xue-Lin,Cao, Yang,Deng, Jun
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supporting information
p. 6052 - 6059
(2017/11/14)
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- Domino Carbopalladation/C-H Functionalization Sequence: An Expedient Synthesis of Bis-Heteroaryls through Transient Alkyl/Vinyl-Palladium Species Capture
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A microwave-assisted highly efficient intermolecular domino carbopalladation/C-H functionalization sequence has been developed to access bis-heteroaryl frameworks in a single operation. The reaction involves carbopalladation of the halogenated acrylamides
- Sharma, Upendra K.,Sharma, Nandini,Kumar, Yogesh,Singh, Brajendra K.,Van Der Eycken, Erik V.
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supporting information
p. 481 - 485
(2016/01/12)
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- Disulfides as Sulfonylating Precursors for the Synthesis of Sulfone-Containing Oxindoles
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The first facile one-pot synthesis of sulfone-containing oxindoles with easily accessible disulfides as the sulfonylating precursors is described. This reaction occurs smoothly under transition metal-free conditions and shows excellent functional group tolerance, allowing the facile and efficient green synthesis of various sulfone-containing oxindoles in aqueous solution. Preliminary mechanistic studies reveal that both water (H2O) and potassium persulfate (K2S2O8) can be the oxygen source of the sulfone groups in the products. (Figure presented.).
- Zhang, Ming-Zhong,Ji, Peng-Yi,Liu, Yu-Feng,Xu, Jing-Wen,Guo, Can-Cheng
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supporting information
p. 2976 - 2983
(2016/09/16)
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- Pd-Catalyzed Highly Regio- and Stereoselective Formation of C-C Double Bonds: An Efficient Method for the Synthesis of Benzofuran-, Dihydrobenzofuran-, and Indoline-Containing Alkenes
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A highly regio- and stereoselective C-C double bond formation reaction via Pd-catalyzed Heck-type cascade process with N-tosylhydrazones has been developed. Various N-tosylhydrazones derived from both ketones and aldehydes are found to be efficient substrates to provide di- and trisubstituted olefins with high regio- and stereoselectivity. Furthermore, this reaction has a good functional group tolerance and different benzofuran-, dihydrobenzofuran-, and indoline-containing alkene products were obtained with high selectivity.
- Gao, Yang,Xiong, Wenfang,Chen, Huoji,Wu, Wanqing,Peng, Jianwen,Gao, Yinglan,Jiang, Huanfeng
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p. 7456 - 7467
(2015/08/18)
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- Domino Heck/borylation sequence towards indolinone-3-methyl boronic esters: trapping of the σ-alkylpalladium intermediate with boron
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Pd-catalyzed domino Heck/borylation of acrylamides with B2pin2 is reported to generate synthetically useful indolinone-3-methyl boronic esters, via capturing σ-alkyl palladium with boron. Further functionalization of the obtained boronic ester qualify it as a new starting point for the functionalization of specific C(sp3)-H bond. Moreover, the application of an Ugi-adduct as starting material or B2nep2 as an alternative boron source works equally well, making this a broadly applicable and robust method for the formation of a C-C and C-B bond in a single operation.
- Vachhani, Dipak D.,Butani, Himanshu H.,Sharma, Nandini,Bhoya, Umed C.,Shah, Anamik K.,Van Der Eycken, Erik V.
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supporting information
p. 14862 - 14865
(2015/10/06)
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- Synthesis of oxindoles through silver-catalyzed trifluoromethylation-, difluoromethylation- and arylsulfonylation-cyclization reaction of N-arylacrylamides
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Efficient synthesis of trifluoromethyl and difluoromethyl-substituted oxindoles was achieved by reacting Langlois reagent or Baran reagent with N-arylacrylamides. However, the reaction of aryl sulfinic acid sodium salts with N-arylacrylamides did not give the desulfinative products, instead, aryl sulfonated products were produced. Copyright
- Liu, Jidan,Zhuang, Shaobo,Gui, Qingwen,Chen, Xiang,Yang, Zhiyong,Tan, Ze
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supporting information
p. 3196 - 3202
(2014/06/09)
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- Pd-catalyzed Heck-type cascade reactions with N-tosyl hydrazones: An efficient way to alkenes via in situ generated alkylpalladium
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A palladium-catalyzed Heck-type cascade reaction of aryl halides and N-tosyl hydrazones is reported. The neopentylpalladium species, generated from an intramolecular Heck-type insertion reaction of aryl halides, could efficiently react with carbenes to fo
- Liu, Xianglei,Ma, Xinna,Huang, Yunze,Gu, Zhenhua
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supporting information
p. 4814 - 4817
(2013/10/08)
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- Direct annulations toward phosphorylated oxindoles: Silver-catalyzed carbon-phosphorus functionalization of alkenes
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Silver screen: The AgNO3-catalyzed carbon phosphorylation of alkenes occurs by an alkene addition/cyclization cascade. Ag+ reacts with Ph2P(O)H to form the crucial active intermediate 1, which promotes the reaction. This method requires a cheap, nontoxic silver salt as the catalyst and substrates for the transformation are simple and readily accessible.
- Li, Ya-Min,Sun, Meng,Wang, Hong-Li,Tian, Qiu-Ping,Yang, Shang-Dong
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supporting information
p. 3972 - 3976
(2013/05/09)
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- A palladium-catalyzed tandem cyclization-cross-coupling reaction using indolylborate as a transfer agent
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Investigation of the palladium-catalyzed tandem cyclization-cross-coupling reaction using indolylborate (2) as a transfer agent has been carried out. Furthermore, the cross-coupling reaction performed under carbon monoxide led to the generation of indolyl
- Ishikura, Minoru,Takahashi, Norinobu,Yamada, Koji,Yanada, Reiko
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p. 11580 - 11591
(2007/10/03)
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- Palladium catalysed tandem cyclisation-anion capture. Part 5: Cascade hydrostannylation-bis-cyclisation-intramolecular anion capture. Synthesis of bridged- and spiro-cyclic small and macrocyclic heterocycles
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A series of O- and N-α,ω-enyne derivatives of 2-iodoarylethers and 2-iodoarylamides undergo palladium catalysed cascade hydrostannylation of the ω-alkyne moiety at 0-25°C followed by bis-cyclisation at 100-110°C terminating in intramolecular sp3-sp2 Stille coupling. These cascades provide a wide range of 5/6 and 5/12-17 membered bicyclic spiro- and bridged-ring heterocycles. (C) 2000 Elsevier Science Ltd.
- Casaschi, Adele,Grigg, Ronald,Sansano, José M,Wilson, David,Redpath, James
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p. 7541 - 7551
(2007/10/03)
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- Palladium Catalysed Tandem Cyclisation-Anion Capture Processes. Part 1. Background and Hydride Ion Capture by Alkyl- and ?-Allyl-Palladium Species.
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A new, wide ranging, synthetically powerful, catalytic tandem cyclisation-anion capture process is proposed which depends on the rate of cyclisation of an organopalladium specifies (RPdX) onto a proximate alkene or diene being significantly faster than an
- Burns, Barry,Grigg, Ronald,Santhakumar, Vijayaratnam,Sridharan, Visuvanathar,Stevenson, Paul,Worakun, Tanachet
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p. 7297 - 7320
(2007/10/02)
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