Rh[III]-Catalyzed C-H Amidation Using Aroyloxycarbamates To Give N-Boc Protected Arylamines

被引：150
作者：
Grohmann, Christoph [1 ]
Wang, Honggen [1 ]
Glorius, Frank [1 ]
机构：
[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 12期
基金：
欧洲研究理事会;
关键词：
CATALYZED DIRECT AMINATION; BOND FORMATION; BORONIC ACIDS; RHODIUM; FUNCTIONALIZATION; ARENES; ACTIVATION; MECHANISM; ALKYNES; AZOLES;
D O I：
10.1021/ol401209f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Rh(III)-catalyzed amidation of C(sp(2))-H bonds by the use of electron-deficient aroyloxycarbamates as efficient electrophilic amidation partners is reported. The reaction proceeded under mild conditions with broad functional group tolerance, and pyridine and O-methyl hydroxamic acids serve as efficient directing groups, giving access to valuable N-Boc protected arylamines (also Fmoc and Cbz). Preliminary mechanistic experiments are discussed.
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收藏
页码：3014 / 3017
页数：4
相关论文
共 82 条
[1]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[2]   C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].
Beccalli, Egle M. ;
Broggini, Gianluigi ;
Martinelli, Michela ;
Sottocornola, Silvia .
CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365
[3]   ORTHO-ACYLHYDROXYLAMINES .1. SYNTHESIS OF ORTHO-BENZOYLHYDROXYLAMINE [J].
CARPINO, LA ;
GIZA, CA ;
CARPINO, BA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (04) :955-957
[4]   O-ACYLHYDROXYLAMINES .2. O-MESITYLENESULFONYL-HYDROXYLAMINE, O-PARA-TOLUENESULFONYL-HYDROXYLAMINE AND O-MESITOYLHYDROXYLAMINE [J].
CARPINO, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (12) :3133-3135
[5]  
Catarzi D., 2012, EUR J MED CHEM, V54, P470
[6]   Rh-Catalyzed Intermolecular Carbenoid Functionalization of Aromatic C-H Bonds by α-Diazomalonates [J].
Chan, Wai-Wing ;
Lo, Siu-Fung ;
Zhou, Zhongyuan ;
Yu, Wing-Yiu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13565-13568
[7]   Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].
Cho, Seung Hwan ;
Kim, Ji Young ;
Kwak, Jaesung ;
Chang, Sukbok .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083
[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]   Transition-Metal-Free Amination of Aryl boronic Acids and Their Derivatives [J].
Coeffard, Vincent ;
Moreau, Xavier ;
Thomassigny, Christine ;
Greck, Christine .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (22) :5684-5686
[10]   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
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