Lewis acid-catalyzed direct amination of benzhydryl alcohols

被引:153
作者
Terrasson, Vincent
Marque, Sylvain
Georgy, Marie
Campagne, Jean-Marc
Prim, Damien
机构
[1] Univ Versailles, CNRS, UMR 8180, Inst Lavoisier, F-78035 Versailles, France
[2] Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
amination; diarylmethylamine; gold; indium; Lewis acid;
D O I
10.1002/adsc.200600236
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The Lewis acid-mediated direct amination of benzylic alcohols is described, providing various benzylic amine derivatives in good yields under mild and environmentally benign conditions. Among the different Lewis acids tested, gold(III) proved to be the catalyst of choice for both chemical (yield, conversion) and practical reasons (a filtration over a silica pad is generally sufficient to obtain the corresponding benzylic amine in analytically pure form).
引用
收藏
页码:2063 / 2067
页数:5
相关论文
共 35 条
[11]  
Dyker G, 2000, ANGEW CHEM INT EDIT, V39, P4237, DOI 10.1002/1521-3773(20001201)39:23<4237::AID-ANIE4237>3.0.CO
[12]  
2-A
[13]   Gold(III) chloride-catalyzed addition reactions of electron-rich arenes to methyl vinyl ketone [J].
Dyker, G ;
Muth, E ;
Hashmi, ASK ;
Ding, L .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (11) :1247-1252
[14]   Gold(III)-catalyzed nucleophilic substitution of propargylic alcohols [J].
Georgy, M ;
Boucard, V ;
Campagne, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (41) :14180-14181
[15]   Asymmetric rhodium-catalyzed hydrogenation meets gold-catalyzed cyclization: Enantioselective synthesis of 8-hydroxytetrahydroisoquinolines [J].
Hashmi, A. Stephen K. ;
Haufe, Patrick ;
Schmid, Christoph ;
Nass, Andreas Rivas ;
Frey, Wolfgang .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (20) :5376-5382
[16]   Gold catalysis:: Proof of arene oxides as intermediates in the phenol synthesis [J].
Hashmi, ASK ;
Rudolph, M ;
Weyrauch, JP ;
Wöelfle, M ;
Frey, W ;
Bats, JW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (18) :2798-2801
[17]  
Hashmi ASK, 2004, GOLD BULL, V37, P51
[18]  
HASHMI ASK, 2006, ADV SYNTH CATAL, V348, P706
[19]   The golden gate to catalysis [J].
Hoffmann-Röder, A ;
Krause, N .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (03) :387-391
[20]   Isoindoles and dihydroisoquinolines by gold-catalyzed intramolecular hydroamination of alkynes [J].
Kadzimirsz, D ;
Hildebrandt, D ;
Merz, K ;
Dyker, G .
CHEMICAL COMMUNICATIONS, 2006, (06) :661-662