CuBr-Catalyzed Reaction of N,N-Dimethylanilines and Silyl Enol Ethers: An Alternative Route to β-Arylamino Ketones

被引:69
作者
Huang, Lehao [1 ]
Zhang, Xunbin [1 ]
Zhang, Yuhong [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
关键词
SP(3) C-H; TERTIARY-AMINES; BONDS ADJACENT; ALIPHATIC-AMINES; MANNICH-BASES; LEWIS-ACID; ACTIVATION; NITROGEN; RUTHENIUM; ARYLATION;
D O I
10.1021/ol901347t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A wide range of silyl enol ethers undergo the reactions with N,N-dimethylanilines in the presence of transition metal catalysts under mild conditions to give beta-arylamino ketones. In the cases of silyl enol ethers derived from unsymmetrical ketones, regiospecific addition of carbonyl compounds was obtained at the olefinic position of silyl enol ether.
引用
收藏
页码:3730 / 3733
页数:4
相关论文
共 46 条
[1]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[2]  
Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO
[3]  
2-E
[4]   A route to annulated indoles via a palladium-catalyzed tandem alkylation/direct arylation reaction [J].
Bressy, C ;
Alberico, D ;
Lautens, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) :13148-13149
[5]   Direct sp3 C-H bond activation adjacent to nitrogen in heterocycles [J].
Campos, Kevin R. .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1069-1084
[6]   A NEW PRACTICAL SYNTHESIS OF SILYL ENOL ETHERS .1. FROM SIMPLE ALDEHYDES AND KETONES [J].
CAZEAU, P ;
DUBOUDIN, F ;
MOULINES, F ;
BABOT, O ;
DUNOGUES, J .
TETRAHEDRON, 1987, 43 (09) :2075-2088
[7]   Ru3(CO)12-catalyzed coupling reaction of sp3 C-H bonds adjacent to a nitrogen atom in alkylamines with alkenes [J].
Chatani, N ;
Asaumi, T ;
Yorimitsu, S ;
Ikeda, T ;
Kakiuchi, F ;
Murai, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) :10935-10941
[8]   RuCl3-Catalyzed Alkenylation of Aromatic C-H Bonds with Terminal Alkynes [J].
Cheng, Kai ;
Yao, Bangben ;
Zhao, Jinlong ;
Zhang, Yuhong .
ORGANIC LETTERS, 2008, 10 (22) :5309-5312
[9]   CuBr-Mediated Oxyalkylation of Vinylarenes under Aerobic Conditions via Cleavage of sp3 C-H Bonds α to Oxygen [J].
Cheng, Kai ;
Huang, Lehao ;
Zhang, Yuhong .
ORGANIC LETTERS, 2009, 11 (13) :2908-2911
[10]   CuBr-Catalyzed Oxidative Difluoromethylation of Tertiary Amines with Difluoroenol Silyl Ethers [J].
Chu, Lingling ;
Zhang, Xingang ;
Qing, Feng-Ling .
ORGANIC LETTERS, 2009, 11 (10) :2197-2200