Iron-Catalyzed C?H and C?C Bond Cleavage: A Direct Approach to Amides from Simple Hydrocarbons

被引:116
作者
Qin, Chong [1 ]
Zhou, Wang [1 ]
Chen, Feng [1 ]
Ou, Yang [1 ]
Jiao, Ning [1 ,2 ]
机构
[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
[2] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
美国国家科学基金会;
关键词
amides; C?H activation; iron; rearrangements; synthetic methods; H AMINATION; RING-EXPANSION; OXIDATIVE AMIDATION; EFFICIENT SYNTHESIS; SCHMIDT REACTION; PRIMARY AZIDES; ALDEHYDES; ARYL; ACTIVATION; CARBON;
D O I
10.1002/anie.201106112
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Something functional: The title reaction proceeds in the presence of azide and water to deliver amides in high yields, and it can be used in a ring-expansion strategy to generate lactams. A mechanism is proposed based on experimental results. This reaction offers a new approach to functionalizing simple and readily available hydrocarbons. DDQ=2,3-dichloro-5,6-dicyano-1,4- benzoquinone. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:12595 / 12599
页数:5
相关论文
共 139 条
[61]   A convenient new procedure for converting primary amides into nitriles [J].
Kuo, Chun-Wei ;
Zhu, Jia-Liang ;
Wu, Jen-Dar ;
Chu, Cheng-Ming ;
Yao, Ching-Fa ;
Shia, Kak-Shan .
CHEMICAL COMMUNICATIONS, 2007, (03) :301-303
[62]  
Lamani M., 2010, ANGEW CHEM, V122, P6772
[63]   An Efficient Oxidation of Primary Azides Catalyzed by Copper Iodide: A Convenient Method for the Synthesis of Nitriles [J].
Lamani, Manjunath ;
Prabhu, Kandikere Ramaiah .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (37) :6622-6625
[64]   Azide rearrangements in electron-deficient systems [J].
Lang, S ;
Murphy, JA .
CHEMICAL SOCIETY REVIEWS, 2006, 35 (02) :146-156
[65]   Intermolecular Dehydrogenative Heck Reactions [J].
Le Bras, Jean ;
Muzart, Jacques .
CHEMICAL REVIEWS, 2011, 111 (03) :1170-1214
[66]   Ring Expansion of Cyclobutylmethylcarbenium Ions to Cyclopentane or Cyclopentene Derivatives and Metal-Promoted Analogous Rearrangements [J].
Leemans, Erika ;
D'hooghe, Matthias ;
De Kimpe, Norbert .
CHEMICAL REVIEWS, 2011, 111 (05) :3268-3333
[67]   Cross-Dehydrogenative Coupling (CDC): Exploring C-C Bond Formations beyond Functional Group Transformations [J].
Li, Chao-Jun .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (02) :335-344
[68]   Cross Dehydrogenative Arylation (CDA) of a Benzylic C-H Bond with Arenes by Iron Catalysis [J].
Li, Yi-Zhou ;
Li, Bi-Jie ;
Lu, Xing-Yu ;
Lin, Song ;
Shi, Zhang-Jie .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (21) :3817-3820
[69]   Palladium-catalyzed intermolecular aerobic oxidative amination of terminal alkenes: Efficient synthesis of linear allylamine derivatives [J].
Liu, Guosheng ;
Yin, Guoyin ;
Wu, Liang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (25) :4733-4736
[70]   [FeIII(F20-tpp)Cl] Is an Effective Catalyst for Nitrene Transfer Reactions and Amination of Saturated Hydrocarbons with Sulfonyl and Aryl Azides as Nitrogen Source under Thermal and Microwave-Assisted Conditions [J].
Liu, Yungen ;
Che, Chi-Ming .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (34) :10494-10501