- Metal free one-pot synthesis of α-ketoamides from terminal alkenes
-
A practical approach towards the synthesis of α-ketoamides from readily available terminal alkenes (styrenes) has been developed. Use of inexpensive I2/2-iodoxybenzoic acid (IBX) in dimethyl sulphoxide (DMSO) as an oxidant under metal free one-pot conditions makes this methodology versatile.
- Dutta, Sayan,Kotha, Surya Srinivas,Sekar, Govindasamy
-
-
Read Online
- Phosphine-free atmospheric carbonylation of aryl iodides with aniline derivatives in the presence of a reusable silica-supported palladium catalyst
-
Various palladium catalysts were obtained by the immobilisation of palladium on silica, modified with imidazolium salts. The efficiency of the catalysts was greatly dependent on the choice of the anion of the imidazolium salt, the palladium precursor and on the conditions of heterogenisation. Palladium acetate immobilised on silica with grafted imidazolium chloride moieties was shown to be a selective and recyclable catalyst for atmospheric aminocarbonylation of aryl iodides with aromatic amines in DMF. It was proved that the greater loss of palladium in DMSO can be explained by the formation of soluble palladium complexes.
- Urbán, Béla,Papp, Máté,Srankó, Dávid,Skoda-F?ldes, Rita
-
-
Read Online
- Aerobic oxidative amidation of alkynes using titanium oxide encapsulated cuprous iodide nanoparticles (CuI@TiO2)
-
A catalyst consisting of titanium oxide encapsulated cuprous iodide nanoparticles was prepared via a sol-gel method using inexpensive raw materials and was harnessed successfully in the oxidative amidation of alkynes via an environmentally benign and sustainable protocol. The mechanism of action of this transformation was thoroughly discussed. The robustness of the catalyst was elucidated by the synthesis of diverse analogues of α-ketoarylamide from a variety of electron rich and poor substrates via a simple procedure in moderate to high yields, with no generation of toxic by-products, in good recyclability up to five cycles, under solvent free and aerobic conditions. The chemical nature, morphology and loading of the CuI@TiO2 nanocatalyst were investigated by TEM, SEM, XPS, EDX, powder XRD, BET, TGA and ICP-MS.
- Dutta, Pratip Kumar,Dhar, Basabbijayi,Sen, Subhabrata
-
-
Read Online
- Facile photochemical synthesis of α-ketoamides and quinoxalines from amines and benzoylacetonitrile under mild conditions
-
A selective protocol for the synthesis of either α-ketoamides or quinoxaline derivatives under the same reaction conditions has been achieved simply by varying substitution number of amino-groups. The method features metal-free, room temperature and broad substrate scopes as well as no extra oxidant. This process applies to various substituent groups and gives products in moderate to good yield. Finally, a rational mechanism was proposed.
- Zhou, Chao,Diao, Pinhui,Li, Xiaoji,Ge, Yanqin,Guo, Cheng
-
-
Read Online
- Double carbonylation of iodoarenes in the presence of reusable palladium catalysts immobilised on supported phosphonium ionic liquid phases
-
The first heterogeneous carbonylation reaction carried out with palladium catalysts immobilised on phosphonium ion modified silica supports is reported. The supported ionic liquid phases were characterised by solid state NMR and FT-IR measurements. The presence of the phosphonium ions on the surface made it possible to carry out double carbonylation in apolar toluene efficiently that resulted in reduced metal leaching. The introduction of dicationic moieties on the solid support has been proved to lead to a further increase in catalyst stability. The catalysts were proved to produce α-ketoamide products with excellent selectivity in the carbonylation of iodoarenes with aliphatic amines while monocarbonylation was the only reaction observed with aniline derivatives. The catalysts could be recycled and used in at least 10 subsequent runs under optimised conditions.
- Urbán, Béla,Szabó, Péter,Srankó, Dávid,Sáfrán, Gy?rgy,Kollár, László,Skoda-F?ldes, Rita
-
-
Read Online
- Palladium-1,10-phenanthroline complex encaged in y zeolite: An efficient and highly recyclable heterogeneous catalyst for aminocarbonylation
-
A promising route for catalytic synthesis of amides by aminocarbonylation of aryl iodides with amines is described using a palladium-1,10-phenanthroline complex encaged in Y zeolite. Complete conversions for aryl iodides and good to excellent yields (71-97%) of various amides were obtained at low Pd loadings of 0.6 mol%. The turnover frequency (TOF) could be up to 139 h-1. A satisfactory yield was obtained even after the catalyst was reused 16 times and the total turnover number (TON) for the 16 cycles was up to 2250. As evidenced by atomic absorption spectrophotometry, UV-vis spectroscopy and X-ray photoelectron spectroscopy, the palladium complex could well nestle down in the supercages of the zeolite without leaching during the recycling process. The significantly enhanced recyclability could be attributed to the double-protection strategy provided by the ligand and the zeolite structure for Pd0 species generated in situ within supercages preventing the migration and leaching of palladium. The supported catalyst has the advantages of easy handing, good to excellent yields, and outstanding recycling capacity for aminocarbonylation reactions of aryl iodides.
- Mei, Hui,Hu, Jianglin,Xiao, Se,Lei, Yizhu,Li, Guangxing
-
-
Read Online
- Stabilized Cu2O nanoparticles on rGO highly catalyzed direct oxidative coupling synthesis of Α-ketoamides with molecular oxygen
-
In this study, a green, efficient, recyclable Cu2O nanoparticles on reduced graphene oxide (Cu2O-NPs@rGO) carbon-based composite catalyst was synthesized by facile one-pot hydrothermal method. And Cu2O-NPs@rGO catalyst was
- Lu, Weiyang,Sun, Wei,Tan, Xiaofeng,Wang, Bin,Yang, Hua,Gao, Lingfeng,Zheng, Gengxiu
-
-
Read Online
- IronO-Catalyzed Domino Aerobic Alcohol Oxidation/Oxidative Cross-Dehydrogenative Coupling for the Synthesis of α-Keto Amides
-
An ironO-catalyzed (TEMPO = 2,2,6,6-tetramethyl-1-piperidinyloxy), aerobic process was developed to synthesize α-keto amides. This reaction proceeds through a domino alcohol oxidation/oxidative cross-dehydrogenative coupling sequence, uses 2-hydroxyacetophenones and amines as the starting materials, and takes place under molecular oxygen, which makes the transformation highly efficient, practical, and environmentally friendly.
- Kotha, Surya Srinivas,Chandrasekar, Selvaraj,Sahu, Samrat,Sekar, Govindasamy
-
-
Read Online
- Phosphine-free double carbonylation of iodobenzene in the presence of reusable supported palladium catalysts
-
Various silica supported palladium catalysts were prepared and tested in the double carbonylation of iodobenzene in the presence of secondary amines. The catalysts were proved to produce α-ketoamide products with excellent selectivity in most cases. At the same time, bulky amines hindered double carbonylation and led to the formation of amides as the main products. Under optimal conditions, the catalysts could be recycled at least six times. An increase in the reaction time led to a decrease in the amount of leached palladium.
- Papp, Máté,Skoda-F?ldes, Rita
-
-
Read Online
- Microwave-assisted direct oxidative synthesis of α-ketoamides from aryl methyl ketones and amines by a water soluble Cu(i)-complex
-
A stable and isolable bis[(tetrabutylammonium) di-μ-iodo-diiododicuprate(i)] complex has been identified for the direct oxidative synthesis of α-ketoamides from substituted aryl methyl ketones and secondary amines in the presence of molecular oxygen. Grat
- Nekkanti, Shalini,Veeramani, Karuna,Praveen Kumar, Niggula,Shankaraiah, Nagula
-
-
Read Online
- Cu(OAc)2 and acids promoted the oxidative cleavage of α-aminocarbonyl compounds with amines: efficient and selective synthesis of 2-t-amino-2-imino-carbonyl and 2-amino-2-oxocarbonyl
-
A novel and efficient method for the synthesis of 2-t-amino-2-imino-carbonyl (C) and 2-amino-2-oxocarbonyl (D) compounds has been discovered through a copper-promoted oxidating amidation reactions between α-amino -carbonyl compounds and amines. Promoted by the crucial copper species, perfect selectivity and good to excellent yields could be achieved. This transformation is achieved through C[sbnd]N bond oxidative cleavage and formation a novel C[sbnd]N bond. This reaction system has a broad reaction scope, providing a facile pathway for the α-functionalization of α-amino ketones.
- Chen, De,Cheng, Chaozhihui,Zeng, Sheng,Luo, Yongyue,Zhang, Jiajia,Deng, Wei,Zeng, Zebing,Wang, Ruijia,Xiang, Jiannan
-
-
Read Online
- Metal free synthesis of α-keto amides from 2-hydroxy acetophenones through domino alcohol oxidation-oxidative amidation reaction
-
An efficient method for the synthesis of α-keto amides using 2-iodoxybenzoic acid (IBX) promoted domino alcohol oxidation and oxidative amidation reaction sequence between 2-oxoalcohols and amines under metal-free conditions is developed. In this protocol, IBX is used as an oxidizing agent to synthesize the α-keto amides, which makes this methodology highly efficient, practical, and environmentally benign.
- Kotha, Surya Srinivas,Sekar, Govindasamy
-
-
Read Online
- One-Pot Synthesis of α-Ketoamides from α-Keto Acids and Amines Using Ynamides as Coupling Reagents
-
A one-pot strategy for α-keto amide bond formation have been developed by using ynamides as coupling reagents under extremely mild reaction conditions. Diversely structural α-ketoamides were afforded in up to 98% yield for 36 examples. This reaction features advantages such as practical coupling procedure, wide functional group tolerance, and extremely mild conditions and has potential applications in synthetic and medicinal chemistry.
- Ma, Jianting,Cui, Xue,Xu, Junyu,Tan, Yinfeng,Wang, Yan,Wang, Xuesong,Li, Youbin
-
supporting information
p. 3661 - 3667
(2022/02/07)
-
- Preparation method of alpha-carbonyl amide compound
-
The invention discloses a preparation method of an alpha-carbonyl amide compound. The method comprises the following steps: under the action of a catalyst, taking oxygen as an oxidant, and carrying out oxidative amidation reaction on an alpha-diazoketone compound shown in a chemical formula 2 and a cyclic secondary amine compound shown in a chemical formula 3 in an organic solvent to obtain the alpha-carbonyl amide compound shown in a chemical formula 1, wherein the formulas 1, 2 and 3 are also shown in the speification. According to the preparation method disclosed by the invention, the alpha-carbonyl amide compound is obtained by taking oxygen as the oxidizing agent and catalyzing alpha-diazoketone and cyclic secondary amine to be subjected to oxidative amidation reaction through cuprous iodide, the reaction condition is mild, the reaction time is short, and the byproduct of the reaction is only nitrogen, so that the method is an effective way for green and efficient preparation of the alpha-carbonyl amide compound.
- -
-
Paragraph 0146-0149
(2021/08/14)
-
- Diversification of α-ketoamides: Via transamidation reactions with alkyl and benzyl amines at room temperature
-
A wide range of N-tosyl α-ketoamides underwent transamidation with various alkyl amines in the absence of a catalyst, base, or additive. On the other hand, transamidation in N-Boc α-ketoamides was achieved in the presence of Cs2CO3. The reactions proceede
- Junaid, Qazi Mohammad,Kandasamy, Jeyakumar,Popuri, Sureshbabu,Sabiah, Shahulhameed,Singh, Shweta
-
p. 7134 - 7140
(2021/08/30)
-
- Pd-Catalyst Containing a Hemilabile P,C-Hybrid Ligand in Amino Dicarbonylation of Aryl Halides for Synthesis of α-Ketoamides
-
The amino dicarbonylation of aryl halides affording α-ketoamides with Pd catalysts is highly dependent on the stereoelectronic properties of the involved ligands. Ionic diphosphine ligand L4 can serve as precursor of a hemilabile P,C (phosphine, carbene)-hybrid ligand to form a stable Pd(II)-complex, Pd-L4. In contrast, analogues L1-L3 with a similar 1-(thiophen-3-yl)-benzimidazolyl skeleton behave as typical (mono/di)phosphines. The catalytic system resulting from the complexation of PdCl2(MeCN)2 and L4 exhibits good catalytic performance in terms of aryl iodides conversion (81-95%) and α-ketoamide selectivity (80-91%), as well as the available recyclability in the RTIL of [Bpy]BF4. The in situ FT-IR analysis reveals that the PdCl2(MeCN)2-L4 catalytic system favors the amino dicarbonylation toward α-ketoamides according to the proposed mechanism of cycle I, which involves two independent CO-insertion steps.
- Yang, Shu-Qing,Yao, Yin-Qing,Chen, Xiao-Chao,Lu, Yong,Zhao, Xiao-Li,Liu, Ye
-
p. 1032 - 1041
(2021/05/07)
-
- Cu-Catalyzed aerobic oxidative cleavage of C(sp3)–C(sp3) bond: Synthesis of α-ketoamides
-
A novel synthesis of α-ketoamides from Cu-catalyzed aerobic oxidative C(sp3)–C(sp3) bond cleavage of hydrocinnamaldehydes has been developed. Readily available and environmentally benign oxygen is used as the oxidant. This reaction avoids the use of noble metal catalysts or specialized oxidants, and chemoselectively yields α-ketoamide. Moreover, based on various control experiments, a reasonable mechanism is proposed.
- Fang, Zheng,Guo, Kai,Liu, Chengkou,Yang, Man,Zhang, Jingming
-
supporting information
(2020/11/02)
-
- Double carbonylation of iodoarenes in the presence of a pyridinium SILP-Pd catalyst
-
The efficiency of a palladium catalyst, immobilised on a supported ionic liquid phase (SILP) with adsorbed 1-butyl-4-methylpyridinium chloride, was investigated in aminocarbonylation reactions. Double carbonylation was found to be the main reaction using different iodoarenes and aliphatic amines as substrates. Application of aniline derivatives as nucleophiles led to the exclusive formation of substituted benzamides. The stabilisation effect of the adsorbed pyridinium ionic liquid was compared to that of imidazolium and phosphonium derivatives. It was proved that the pyridinium SILP-palladium catalyst could be reused in at least 10 cycles. Recyclability was tested in five successive runs for all of the substrates.
- Nagy, Enik?,Nagy, Petra,Papp, Máté,Skoda-F?ldes, Rita,Urbán, Béla
-
-
- Cu-Catalysed oxidative amidation of cinnamic acids/arylacetic acids with 2° amines: An efficient synthesis of α-ketoamides
-
A new and convenient copper-catalysed synthesis of α-ketoamides has been accomplished using readily available cinnamic acids/arylacetic acids and 2° amines in an open atmosphere. The reaction between cinnamic acid and amine involves the formation of enamine followed by its aerobic oxidation, whereas the reaction of arylacetic acid with amine involves amide formation followed by benzylic methylene oxidation.
- Sharma, Anup Kumar,Jaiswal, Anjali,Singh, Krishna Nand
-
supporting information
p. 9348 - 9351
(2019/11/11)
-
- Metal-Free C=C Double Bond Cleavage on Enaminones for the Synthesis of α-Ketoamides by Free-Radical Aerobic Oxygenation
-
The tandem oxidation of the enaminone C=C double bond as well as subsequent C-N bond formation are realized under metal-free conditions by thermo-induced free radical transformation. In the presence of benzoyl peroxide (BPO) and N-iodosuccinimide (NIS), a
- Yang, Yiming,Zhong, Guofeng,Fan, Junfen,Liu, Yunyun
-
supporting information
p. 4422 - 4425
(2019/06/24)
-
- Copper-catalyzed oxidative synthesis of 2-oxo-acetamidines from one-pot three-component reaction of aryl methyl ketones, secondary amines and anilines
-
Some novel 2-oxo-acetamidines were synthesized via one-pot three-component reaction of acetophenones, secondary amines and anilines in presence of CuI as catalyst. The reaction involved in a oxidation process of C (sp3)–H bonds of acetophenones
- Dutta, Leema,Bhuyan, Pulak J.
-
p. 5770 - 5778
(2018/08/22)
-
- Cu(i)/{Nb6O19} catalyzed: N -acylation of arylacetic acids with amines under aerobic conditions
-
The method described herein is a general, efficient and green approach to synthesize α-ketoamides from arylacetic acids and amines. Employing a simple copper(i)/{Nb6O19} catalyst system, the reaction offers a facile process to give functionalized α-ketoamides from readily available arylacetic acids under aerobic conditions. The merit of this new strategy is that it expands the syntheses of α-ketoamides from stable, inexpensive and widely available acylation reagents such as arylacetic acids in one step.
- Li, Pei-He,Wang, Zheng,Fu, Hui,Dai, Qi-Pu,Hu, Chang-Wen
-
supporting information
p. 12471 - 12474
(2018/11/23)
-
- UV Assisted High-Efficient Synthesis of α-Ketoamides using Air Promoted by A Non-Metal Catalyst in Aqueous Solution
-
Presented here is the first example of UV (λ=210 nm) promoted procedure proceeding in aqueous media at room temperature using ambient air as the oxidant for efficient synthesis of an array of α-ketoamides of all types using a non-metal catalyst N-iodosuccinimide with a loading of 20 mol%. With UV, oxygen in the air was efficiently utilized as the green oxidant, some control experiments were carried out and a plausible mechanism was proposed, disclosing that in aqueous solution, the oxidation process was actually triggered by dioxygen radical anion (O2.?), while not molecular oxygen. A variety of secondary amines and primary amines as well as ammonia were employed as the amine moieties, and the desired product primary-, secondary-, and tertiary α-ketoamides were afforded in good to excellent yields of up to 96 %.
- Li, Jianhui,He, Shaopo,Zhang, Kuan,Quan, Ziyi,Shan, Qiheng,Sun, Zhongliang,Wang, Bo
-
p. 4868 - 4873
(2018/10/15)
-
- Solvent-free one-pot oxidation of ethylarenes for the preparation of α-ketoamides under mild conditions
-
Here we developed a highly efficient solvent-free, one-pot procedure for synthesizing α-ketoamides from ethylarenes and amines, by oxidizing a C-H bond sp3 center. A copper catalyst was employed, and the reactions proceeded smoothly at ambient temperatures. Most of the tested ethylarenes and amines were successfully converted to their corresponding α-ketoamides in moderate to excellent yields of up to 93% with three equivalents of the oxidant tert-butyl hydroperoxide.
- Liu, Fuyan,Zhang, Kuan,Liu, Yanfeng,Chen, Shan,Chen, Yiping,Zhang, Dela,Lin, Chunfu,Wang, Bo
-
p. 7158 - 7162
(2017/02/05)
-
- Flexible and Chemoselective Oxidation of Amides to α-Keto Amides and α-Hydroxy Amides
-
A suite of flexible and chemoselective methods for the transition-metal-free oxidation of amides to α-keto amides and α-hydroxy amides is presented. These highly valuable motifs are accessed in good to excellent yields and stereoselectivities with high functional group tolerance. The utility of the method is showcased by the formal synthesis of a potent histone deacetylase inhibitor.
- De La Torre, Aurélien,Kaiser, Daniel,Maulide, Nuno
-
p. 6578 - 6581
(2017/05/29)
-
- Direct Aerobic Oxidative Reactions of 2-Hydroxyacetophenones
-
Valuable and direct aerobic oxidation reactions of 2-hydroxyacetophenones were explored. The concept was based on the in situ treatment of small quantities of aerobically formed α-keto aldehydes that drove the reactions to the corresponding products. This new strategy was applied for a variety of oxidative reactions of 2-hydroxyacetophenones, and valuable products such as phthalides, quinoxalines, and α-keto amides were obtained in good to high yields.
- Sahoo, Subas Chandra,Nath, Utpal,Pan, Subhas Chandra
-
supporting information
p. 4434 - 4438
(2017/08/23)
-
- Mono- and double carbonylation of aryl iodides with amine nucleophiles in the presence of recyclable palladium catalysts immobilised on a supported dicationic ionic liquid phase
-
Silica modified with organic dicationic moieties proved to be an excellent support for palladium catalysts used in the aminocarbonylation of aryl iodides. By an appropriate choice of the reaction conditions, the same catalyst could be used for selective mono- or double carbonylations leading to amide and α-ketoamide products, respectively. The best catalyst could be recycled for at least 10 consecutive runs with a loss of palladium below the detection limit. By the application of the new support, efficient catalyst recycling could be achieved under mild reaction conditions (under low pressure and in a short reaction time). Palladium-leaching data support a mechanism with dissolution - re-precipitation of the active palladium species.
- Papp,Szabó,Srankó,Sáfrán,Kollár,Skoda-F?ldes
-
p. 44587 - 44597
(2017/09/26)
-
- Synthesis of α-Keto Amides by a Pyrrolidine/TEMPO-Mediated Oxidation of α-Keto Amines
-
A mild procedure has been developed for the synthesis of α-keto amides by α-oxidation of the corresponding α-keto amines mediated by pyrrolidine and TEMPO. The method can also be applied to the synthesis of α-keto thioamides and α-keto amidines.
- Yu, Lu,Somfai, Peter
-
supporting information
p. 2587 - 2590
(2016/11/11)
-
- One pot synthesis of α-ketoamides from ethylarenes and amines: a metal free difunctionalization strategy
-
One-pot and metal free synthesis of α-ketoamides has been described through in situ generation of aryl ketones from easily available ethylarenes followed by amidation with various amines. This multiple oxidation protocol involves catalytic I2-pyridine-TBHP (t-butyl hydroperoxide) mediated oxidative benzylic carbonylation and sequential NaI-TBHP mediated oxidative amidation without using any solvent.
- Ramanathan, Mani,Kuo, Chun-Kai,Liu, Shiuh-Tzung
-
p. 11446 - 11453
(2016/12/16)
-
- Room temperature copper-catalyzed oxidative amidation of terminal alkynes for the synthesis of α-ketoamides using: O -benzoyl hydroxylamines as aminating reagent and oxidant
-
A novel and convenient copper-catalyzed oxidative amidation for the synthesis of α-ketoamides has been successfully developed, which uses easily available O-benzoyl hydroxylamines as aminating reagent and oxidant. The reaction proceeds smoothly at room temperature and is compatible with a range of substrates to give the desired products in moderate to good yields.
- Shen, Guodong,Zhao, Lingyu,Wang, Yichen,Zhang, Tongxin
-
p. 78307 - 78310
(2016/09/09)
-
- Copper-TEMPO-catalyzed synthesis of α-ketoamides: Via tandem sp3C-H aerobic oxidation and amination of phenethyl alcohol derivatives
-
An efficient copper-TEMPO-catalyzed one-pot synthesis of α-ketoamides from phenethyl alcohol derivatives was developed firstly. Moreover, molecular oxygen in open air was employed as the oxidant with a broad substrate scope, which makes this methodology more practical. Based on some control experiments, a plausible mechanism was proposed.
- Liu, Chengkou,Yang, Zhao,Guo, Shiyu,Zeng, Yu,Zhu, Ning,Li, Xin,Fang, Zheng,Guo, Kai
-
supporting information
p. 8570 - 8575
(2016/09/28)
-
- A two-step continuous synthesis of α-ketoamides and α-amino ketones from 2° benzylic alcohols using hydrogen peroxide as an economic and benign oxidant
-
A practical two-step synthesis of α-ketoamides and α-amino ketones via direct oxidative coupling between 2° benzylic alcohols and amines was developed. Hydrogen peroxide, an economic and environmentally friendly oxidant, was used, and a metal catalyst was unnecessary. Moreover, the continuous-flow technique was employed to increase the functional group tolerance, efficiency and safety.
- Liu, Chengkou,Fang, Zheng,Yang, Zhao,Li, Qingwen,Guo, Shiyu,Guo, Kai
-
p. 25167 - 25172
(2016/03/22)
-
- Copper-catalyzed, hypervalent iodine mediated C=C bond activation of enaminones for the synthesis of α-keto amides
-
An unprecedented C=C bond cleavage of enaminones has been realized by means of copper catalysis in the presence of hypervalent iodine (PhI(OAc)2). The cascade transformation based on this bond cleavage leads to the synthesis of various α-keto amides. Isotope labeling experiments suggest that water has acted as a source of oxygen atoms during the generation of the new carbonyl group.
- Wan, Jie-Ping,Lin, Yunfang,Cao, Xiaoji,Liu, Yunyun,Wei, Li
-
supporting information
p. 1270 - 1273
(2016/01/15)
-
- I2-promoted aerobic oxidative coupling of acetophenes with amines under metal-free conditions: Facile access to α-ketoamides
-
A novel and efficient I2-promoted oxidative coupling of acetophenes with amines to α-ketoamides is presented, which employs O2 as an environmentally friendly oxidant under metal-free conditions. Based on a series of control experimen
- Guo, Shiyu,Fang, Zheng,Yang, Zhao,Liu, Chengkou,Dai, Zhongxue,Zhao, Lihuan,Guo, Kai
-
p. 1503 - 1507
(2016/01/16)
-
- Cu(i)-Functionalized SBA-16: An efficient catalyst for the synthesis of α-ketoamides under moderate conditions
-
An efficient catalyst based on the cage-like mesoporous material SBA-16 as the support and Cu(i) as active sites has been successfully prepared. The catalyst demonstrated high catalytic activity (up to 88%) in the direct oxidative synthesis of α-ketoamides between acetophenone and piperidine, employing O2 from open air as the oxidant without other additives. A heterogeneous catalyst was applied in this reaction for the first time, and the catalyst could be easily separated from the reaction system by filtration and reused several times without a significant loss of activity.
- Zhang, Xueyao,Yang, Honglei,Huo, Yong,Li, Jing,Ma, Jianxin,Ma, Jiantai
-
p. 8972 - 8983
(2016/06/09)
-
- TBAI-catalyzed synthesis of α-ketoamides via sp3 C-H radical/radical cross-coupling and domino aerobic oxidation
-
A TBAI-catalyzed one-pot synthesis of α-ketoamides via sp3 C-H radical/radical cross-coupling and domino aerobic oxidation was developed. This synthesis is suitable for abroad range of substrates. The control experiments suggested a possible oxidative coupling mechanism.
- Fan, Weizheng,Shi, Dongyang,Feng, Bainian
-
p. 4638 - 4641
(2015/07/02)
-
- Direct Regioselective Oxidative Cross-Coupling of Indoles with Methyl Ketones: A Novel Route to C3-Dicarbonylation of Indoles
-
The first C3-dicarbonylation of indoles was realized through direct oxidative cross-coupling of indoles with methyl ketones in the presence of molecular iodine and pyrrolidine. This reaction constructed a highly efficient indolyl diketones scaffold, which
- Gao, Qinghe,Zhang, Jingjing,Wu, Xia,Liu, Shan,Wu, Anxin
-
p. 134 - 137
(2015/07/28)
-
- Iodine-promoted oxidative amidation of terminal alkenes - Synthesis of α-ketoamides, benzothiazoles, and quinazolines
-
A novel metal-free strategy for oxidative amidation of terminal alkenes by using I2/DMSO for the synthesis of α- ketoamides has been developed. Intriguingly, the use of tertbutylhydroperoxide (TBHP) as co-oxidant can facilitate the synthesis of α-ketoamides at room temperature without any solvent, thereby making it a green protocol. The reaction with primary amines can be easily achieved by using SeO2 as an oxidizing agent. Besides, the scope of the method was also extended to the synthesis of benzothiazolines and quinazolines.
- Deshidi, Ramesh,Devari, Shekaraiah,Shah, Bhahwal Ali
-
supporting information
p. 1428 - 1432
(2015/03/04)
-
- Benzoylformamides as new photocaged bases for photo-latent anion polymerization
-
Benzoylformamide (BFA) derivatives are proposed as new photocaged bases with good solubility in epoxy resin. Initially their structures were confirmed by 1H NMR, 13C NMR, and elemental analysis. Next, we detail their thermal stability, solubility behavior, and photolysis products. Furthermore, the model photo-latent anion polymerization (AP) of epoxide system in the presence of BFA-dBA (N,N-dibenzyl-2-oxo-2-phenylacetamide) as a photocaged base has been investigated, and excellent photopolymerization profile is obtained.
- He, Ming-Hui,Su, Mei-Lin,Yu, Zhao-Hui,Chen, Guang-Xue,Zeng, Zhao-Hua,Yang, Jian-Wen
-
-
- A general metal free approach to α-ketoamides via oxidative amidation-diketonization of terminal alkynes
-
A novel catalytic system TMSOTf/I2/DMSO for the oxidative coupling of terminal alkynes with virtually any primary/secondary amine leading to α-ketoamides has been developed. The reaction possibly proceeds via iminium ion formation, wherein DMSO acts as a solvent as well as an oxidizing agent. This journal is the Partner Organisations 2014.
- Deshidi, Ramesh,Kumar, Manjeet,Devari, Shekaraiah,Shah, Bhahwal Ali
-
supporting information
p. 9533 - 9535
(2014/08/18)
-
- Metal-free oxidative amidation of 2-oxoaldehydes: A facile access to α-ketoamides
-
A novel and efficient method for the synthesis of α-ketoamides, employing a dimethyl sulfoxide (DMSO)-promoted oxidative amidation reaction between 2-oxoaldehydes and amines under metal-free conditions is presented. Furthermore, mechanistic studies supported an iminium ion-based intermediate as a central feature of reaction wherein C1-oxygen atom of α-ketoamides is finally derived from DMSO.
- Mupparapu, Nagaraju,Khan, Shahnawaz,Battula, Satyanarayana,Kushwaha, Manoj,Gupta, Ajai Prakash,Ahmed, Qazi Naveed,Vishwakarma, Ram A.
-
p. 1152 - 1155
(2014/03/21)
-
- Stability or flexibility: Metal nanoparticles supported over cross-linked functional polymers as catalytic active sites for hydrogenation and carbonylation
-
A novel cross-linked functional polymer was prepared through copolymerization between 1, 3, 4, 6-tetraallylglycoluril and 4-vinyl pyridine. Pt and Pd nanoparticles supported over this polymeric framework (Pt/CFP and Pd/CFP) were detailedly characterized by TEM, EDS, and XPS. Pt nanoparticles were kept in the monodispersed state with the average size of 1.4 nm. Monodispersed Pd nanoparticles were about 4.5 nm. The hydrogenation of nitrobenzenes over Pt/CFP shows high activity and selectivity with the substrate to Pt ratio of 4000 under mild reactions. Pd/CFP was the catalyst for carbonylation of aryl iodides in the presence of secondary amines and acylhydrazines. Double carbonylation with secondary amines produced α-ketoamides with the selectivity of 80%. Diacylhydrazine molecules were synthesized by the direct carbonylation of aryl iodide with acylhydrazine over Pd/CFP. The recyclability and recoverability of Pt/CFP were investigated through a seven-run recycling test of nitrobenzene hydrogenation. The flexibility of Pd/CFP in the carbonylation process was thoroughly explored by a 12-run recycling test. Supported Pt or Pd nanoparticles showed the macroscopic robustness in their catalytic performance in the catalytic cycle. The flexibility of metal nanoparticles and the polymeric supports guaranteed macroscopic catalytic robustness.
- Chen, Bingfeng,Li, Fengbo,Huang, Zhijun,Lu, Tao,Yuan, Guoqing
-
-
- Chemical conversion of β-O-4 lignin linkage models through Cu-catalyzed aerobic amide bond formation
-
Methods for conversion of the lignin β-O-4 models into amide derivatives and phenols have been developed, which is achieved via chemo-selective oxidation of the secondary benzylic alcohol and subsequent Cu-catalyzed aerobic amide bond formation.
- Zhang, Jian,Liu, Yu,Chiba, Shunsuke,Loh, Teck-Peng
-
supporting information
p. 11439 - 11441
(2013/12/04)
-
- A facile protocol for N-alkylation of azoles using KOtBu as base under NBS-promoted conditions
-
A mild, transition metal-free, and environmentally benign NBS-promoted C-N bond formation of N-heterocycles is successfully demonstrated. A series of heterocyclic derivatives are readily prepared under mild conditions in moderate to good yields.
- Chen, Wen-Lin,Li, Ji-Hui,Meng, Xu,Tang, Dong,Guo, Shuai-Bo,Chen, Bao-Hua
-
supporting information
p. 295 - 299
(2013/02/25)
-
- Simplified procedure for TEMPO-catalyzed oxidation: Selective oxidation of alcohols, α-hydroxy esters, and amides using TEMPO and calcium hypochlorite
-
A wide range of primary and secondary multifunctional alcohols, α-hydroxyamides, and α-hydroxyesters were oxidized to their corresponding aldehydes, ketones, α-ketoamides, and α-ketoesters under mild reaction conditions using 2,2,6,6-tetramethylpiperidine-1-oxyl as a catalyst with calcium hypochlorite as an oxidant [TEMPO-Ca(OCl)2]. This simplified method does not require any transition metals, acids, or bases and demonstrates controlled and selective oxidation of structurally diverse alcohols, affording moderate to excellent yields at room temperature.
- Reddy, Sabbasani Rajasekhara,Stella, Selvaraj,Chadha, Anju
-
experimental part
p. 3493 - 3503
(2012/09/22)
-
- Biocatalytic reduction of α-keto amides to (R)-α-hydroxy amides using Candida parapsilosis ATCC 7330
-
Biocatalytic reduction of primary and secondary α-keto amides was accomplished using whole cells of Candida parapsilosis ATCC 7330. The primary (R)-α-hydroxy amides were obtained in good enantiomeric excess (up to 94%) and conversion (88-99%) as compared to the secondary (R)-α-hydroxy amides.
- Stella, Selvaraj,Chadha, Anju
-
p. 345 - 352
(2013/01/15)
-
- Coupling of methyl ketones and primary or secondary amines leading to α-ketoamides
-
A metal-free oxidative coupling of methyl ketones and primary or secondary amines to α-ketoamides has been developed. Four intermediates, α-iodoketone, α-aminoketone, iminium intermediate, and α-hydroxy amine have been identified through a series of control experiments. The atom-economic methodology can be scaled-up, tolerates a variety of functional groups, and is operationally simple.
- Wei, Wei,Shao, Ying,Hu, Huayou,Zhang, Feng,Zhang, Chao,Xu, Yuan,Wan, Xiaobing
-
p. 7157 - 7165
(2012/11/07)
-
- Copper-catalyzed aerobic oxidative synthesis of α-ketoamides from methyl ketones, amines and NIS at room temperature
-
A simple, efficient and practical copper-catalyzed aerobic oxidative synthesis of α-ketoamides from aryl methyl ketones, aliphatic amines and N-iodosuccinimide (NIS) has been developed. The one-pot reaction may proceed smoothly at room temperature in the open air. The possible mechanism for the formation of α-ketoamides was proposed. Molecular oxygen in air functions as both an oxidant and an oxygen source.
- Zhang, Juan,Wei, Ying,Lin, Shaoxia,Liang, Fushun,Liu, Pengjun
-
p. 9237 - 9242
(2013/01/15)
-
- NIS-catalyzed reactions: Amidation of acetophenones and oxidative amination of propiophenones
-
Single-step amination: The N-iodosuccinimide (NIS)-catalyzed amidation of acetophenone derivatives by using tert-butylhydroperoxide (TBHP) as an oxidant is presented. A variety of acetyl derivatives of heterocyclic compounds were easily converted to their corresponding ketoamides under these conditions. A new, NIS-catalyzed amination of propiophenone and its derivatives in the presence of TBHP to furnish the corresponding 2-aminoketone derivatives is the first reported single-step amination of propiophenone derivatives. Copyright
- Lamani, Manjunath,Prabhu, Kandikere Ramaiah
-
supporting information
p. 14638 - 14642
(2013/01/15)
-