- One-Pot Synthesis of α-Branched N-Acylamines via Titanium-Mediated Condensation of Amides, Aldehydes, and Organometallics
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A three-component, titanium-mediated synthesis of α-branched N-acylamines from commercial or readily accessible amides, aldehydes, and organometallic reagents is reported. The transformation proceeds under mild reaction conditions and tolerates a variety of functional groups (including nitrile, carbamate, olefin, basic amine, furan, and other sensitive heteroaromatics) to generate a large umbrella of α-branched N-acylamine products in high yields. The operationally practical procedure enables the use of this method in parallel chemical synthesis, a valuable feature that can facilitate the screening of bioactive molecules by medicinal chemists.
- Dai, Chunhui,Genovino, Julien,Bechle, Bruce M.,Corbett, Matthew S.,Huh, Chan Woo,Rose, Colin R.,Sun, Jianmin,Warmus, Joseph S.,Blakemore, David C.
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supporting information
p. 1064 - 1067
(2017/03/15)
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- Copper-Catalyzed Reductive N-Alkylation of Amides with N-Tosylhydrazones Derived from Ketones
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A CuI-catalyzed reductive coupling of ketone-derived N-tosylhydrazones with amides is presented. Under the optimized conditions, an array of N-tosylhydrazones derived from aryl–alkyl and diaryl ketones could couple effectively with a wide variety of (hete
- Xu, Peng,Qi, Fu-Ling,Han, Fu-She,Wang, Yan-Hua
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p. 2030 - 2034
(2016/07/28)
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- Copper-Catalyzed Ligand-Free Amidation of Benzylic Hydrocarbons and Inactive Aliphatic Alkanes
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An efficient copper-catalyzed amidation of benzylic hydrocarbons and inactive aliphatic alkanes with simple amides was developed. The protocol proceeded smoothly without any ligand, and a wide range of N-alkylated aromatic and aliphatic amides, sulfonamides, and imides were synthesized in good yields.
- Zeng, Hui-Ting,Huang, Jing-Mei
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p. 4276 - 4279
(2015/09/15)
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- Au(iii)-catalyzed intermolecular amidation of benzylic C-H bonds
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Au(iii)-catalyzed intermolecular amidations of benzylic C-H bonds with sulfonamides and carboxamides are described. The protocol with the Au-bipy complex/N-bromosuccinimide system provides practical applications for synthesis of various amides via C-H activations. The reaction proceeds with high efficiency to give the corresponding amines, which are extremely useful synthetic intermediates.
- Zhang, Yan,Feng, Bainian,Zhu, Chengjian
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supporting information
p. 9137 - 9141,5
(2012/12/12)
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- Cobalt-catalyzed benzylic C-H amination via dehydrogenative-coupling reaction
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An efficient direct benzylic C-H amination via dehydrogenative-coupling by using an inexpensive catalyst/oxidant (CoBr2/tBuOO tBu) system is described. Various unmodified amides including primary or secondary sulfonamides, carboxamides, and carbamates preformed well with benzylic hydrocarbons with moderate to good yields.
- Ye, Yang-Hong,Zhang, Ji,Wang, Gao,Chen, Shan-Yong,Yu, Xiao-Qi
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supporting information; experimental part
p. 4649 - 4654
(2011/06/27)
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- Secondary benzylation with benzyl alcohols catalyzed by a high-valent heterobimetallic Ir-Sn complex
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(Chemical Equation Presented) A highly efficient secondary benzylation procedure has been demonstrated using a high-valent heterobimetallic complex [Ir2(COD)2(SnCls)2(Cl)2(μ-Cl) 2] 1 as the catalyst in 1,2-dichloroethane to afford the corresponding benzylated products in moderate to excellent yields. The reaction was performed not only with carbon nucleophiles (arenes and heteroarenes) but also with oxygen (alcohol), nitrogen (amide and sulfonamide), and sulfur (thiol) nucleophiles. Mechanistic investigation showed the intermediacy of the ether in this reaction. An electrophilic mechanism is proposed from Hammett correlation.
- Podder, Susmita,Choudhury, Joyanta,Roy, Sujit
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p. 3129 - 3132
(2008/02/07)
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- Platinum-catalyzed intermolecular hydroamination of vinyl arenes with carboxamides
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(Chemical Equation Presented) Reaction of benzamide with 4-methylstyrene catalyzed by a 1:2 mixture of [PtCl2(H2C=CH 2)]2 and P(4-C6H4CF 3)3 (5 mol %) in mesitylene at 140 °C for 24 h led to the isolation of N-(1-p-tolylethyl)benzamide in 85% yield. Electron-rich, electron-poor, and hindered vinyl arenes underwent Markovnikov hydroamination with a range of carboxamides and amide derivatives in moderate to good yield with excellent regioselectivity.
- Qian, Hua,Widenhoefer, Ross A.
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p. 2635 - 2638
(2007/10/03)
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