Copper-Catalyzed Ligand-Free Amidation of Benzylic Hydrocarbons and Inactive Aliphatic Alkanes

被引:73
作者
Zeng, Hui-Ting [1 ]
Huang, Jing-Mei [1 ]
机构
[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H BONDS; METAL-FREE; CHLORAMINE-T; AMINATION; FUNCTIONALIZATION; C(SP(3))-H; AMIDES; INSERTION; SULFOXIMINES; SULFONAMIDES;
D O I
10.1021/acs.orglett.5b02063
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:4276 / 4279
页数:4
相关论文
共 39 条
[1]   Amination of ethers using chloramine-T hydrate and a copper(I) catalyst [J].
Albone, DP ;
Challenger, S ;
Derrick, AM ;
Fillery, SM ;
Irwin, JL ;
Parsons, CM ;
Takada, H ;
Taylor, PC ;
Wilson, DJ .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (01) :107-111
[2]   Copper-Nitrene Complexes in Catalytic C-H Amination [J].
Badiei, Yosra M. ;
Dinescu, Adriana ;
Dai, Xiliang ;
Palomino, Robert M. ;
Heinemann, Frank W. ;
Cundari, Thomas R. ;
Warren, Timothy H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (51) :9961-9964
[3]   Efficient copper-catalyzed benzylic amidation with anhydrous chloramine-T [J].
Bhuyan, Ranjana ;
Nicholas, Kenneth M. .
ORGANIC LETTERS, 2007, 9 (20) :3957-3959
[4]   tert-Butyl peroxybenzoate (TBPB)-mediated 2-isocyanobiaryl insertion with 1,4-dioxane: efficient synthesis of 6-alkyl phenanthridines via C(sp3)-H/C(sp2)-H bond functionalization [J].
Cao, Jia-Jia ;
Zhu, Tong-Hao ;
Wang, Shun-Yi ;
Gu, Zheng-Yang ;
Wang, Xiang ;
Ji, Shun-Jun .
CHEMICAL COMMUNICATIONS, 2014, 50 (49) :6439-6442
[5]   Selective functionalisation of saturated C-H bonds with metalloporphyrin catalysts [J].
Che, Chi-Ming ;
Lo, Vanessa Kar-Yan ;
Zhou, Cong-Ying ;
Huang, Jie-Sheng .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) :1950-1975
[6]   Iron-Catalyzed Hetero-Cross-Dehydrogenative Coupling Reactions of Sulfoximines with Diarylmethanes: A New Route to N-Alkylated Sulfoximines [J].
Cheng, Ying ;
Dong, Wanrong ;
Wang, Long ;
Parthasarathy, Kanniyappan ;
Bolm, Carsten .
ORGANIC LETTERS, 2014, 16 (07) :2000-2002
[7]   Metal-free oxidative direct C(sp3)-H bond functionalization of ethers with α,α-diaryl allylic alcohols [J].
Chu, Xue-Qiang ;
Meng, Hua ;
Zi, You ;
Xu, Xiao-Ping ;
Ji, Shun-Jun .
CHEMICAL COMMUNICATIONS, 2014, 50 (68) :9718-9721
[8]   Catalytic C-H amination: the stereoselectivity issue [J].
Collet, Florence ;
Lescot, Camille ;
Dauban, Philippe .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) :1926-1936
[9]   Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion [J].
Davies, Huw M. L. ;
Manning, James R. .
NATURE, 2008, 451 (7177) :417-424
[10]   Coinage metal catalyzed C-H bond functionalization of hydrocarbons [J].
Diaz-Requejo, M. Mar ;
Perez, Pedro J. .
CHEMICAL REVIEWS, 2008, 108 (08) :3379-3394