Rhodium(III)-Catalyzed Intermolecular Direct Amination of Aromatic C-H Bonds with N-Chloroamines

被引:200
作者
Ka-Ho Ng
Zhou, Zhongyuan
Yu, Wing-Yiu [1 ]
机构
[1] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, State Key Lab Chirosci, Hong Kong, Hong Kong, Peoples R China
关键词
CATALYZED DIRECT AMINATION; CROSS-COUPLING REACTION; STEREOSELECTIVE-SYNTHESIS; ARYL; ACTIVATION; AMIDATION; RH; FUNCTIONALIZATION; ALDEHYDES; ALKYNES;
D O I
10.1021/ol203046n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Rh(III)-catalyzed direct aromatic C-H amination is achieved using N-chloroamines as a reagent. Furthermore, we also developed a one-pot amination protocol Involving In situ chlorination of the secondary amines. The catalytic amination operates at mild conditions with excellent functional group tolerance and regioselectivity.
引用
收藏
页码:272 / 275
页数:4
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共 65 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]   Direct Azole Amination: C-H Functionalization as a New Approach to Biologically Important Heterocycles [J].
Armstrong, Alan ;
Collins, James C. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (13) :2282-2285
[3]   Umpolung Amination: Nickel-Catalyzed Coupling Reactions of N,N-Dialkyl-N-chloroamines with Diorganozinc Reagents [J].
Barker, Timothy J. ;
Jarvo, Elizabeth R. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (43) :15598-+
[4]   (BENZOYLPHENYL)PIPERIDINES - A NEW CLASS OF IMMUNOMODULATORS [J].
BELLAMY, FD ;
CHAZAN, JB ;
DODEY, P ;
DUTARTRE, P ;
OU, K ;
PASCAL, M ;
ROBIN, J .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (05) :1545-1552
[5]   Pd-Catalyzed Ortho-C HAcylation/Cross Coupling of Aryl Ketone O-Methyl Oximes with Aldehydes Using tert-Butyl Hydroperoxide as Oxidant [J].
Chan, Chun-Wo ;
Zhou, Zhongyuan ;
Chan, Albert S. C. ;
Yu, Wing-Yiu .
ORGANIC LETTERS, 2010, 12 (17) :3926-3929
[6]   Ruthenium Catalyzed Directing Group-Free C2-Selective Carbenoid Functionalization of Indoles by α-Aryldiazoesters [J].
Chan, Wai-Wing ;
Yeung, Shing-Hin ;
Zhou, Zhongyuan ;
Chan, Albert S. C. ;
Yu, Wing-Yiu .
ORGANIC LETTERS, 2010, 12 (03) :604-607
[7]   Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].
Chen, Xiao ;
Engle, Keary M. ;
Wang, Dong-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115
[8]   Silver-Mediated Direct Amination of Benzoxazoles: Tuning the Amino Group Source from Formamides to Parent Amines [J].
Cho, Seung Hwan ;
Kim, Ji Young ;
Lee, S. Yunmi ;
Chang, Sukbok .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (48) :9127-9130
[9]   Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].
Colby, Denise A. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
CHEMICAL REVIEWS, 2010, 110 (02) :624-655
[10]   Catalytic C-H amination: recent progress and future directions [J].
Collet, Florence ;
Dodd, Robert H. ;
Dauban, Philippe .
CHEMICAL COMMUNICATIONS, 2009, (34) :5061-5074