FeCl3-catalyzed Ritter reaction. Synthesis of amides

被引:88
作者
Anxionnat, Bruno [1 ]
Guerinot, Amandine [1 ]
Reymond, Sebastien [1 ]
Cossy, Janine [1 ]
机构
[1] ESPCI ParisTech, CNRS, Chim Organ Lab, F-75231 Paris 05, France
关键词
Ritter reaction; Nitriles; Amides; Iron; N-TERT-BUTYL; ALLYLIC ALCOHOLS; EFFICIENT; ALKYLATION; AMIDATION; SECONDARY; NITRILES;
D O I
10.1016/j.tetlet.2009.02.208
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A safe and inexpensive synthesis of amides, from benzylic alcohols and nitriles and from t-butyl acetate and nitriles, using a Ritter reaction catalyzed by FeCl3 center dot 6H(2)O is described. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3470 / 3473
页数:4
相关论文
共 19 条
[1]   o-Benzenedisulfonimide as a Reusable Bronsted Acid Catalyst for Ritter-Type Reactions [J].
Barbero, Margherita ;
Bazzi, Stefano ;
Cadamuro, Silvano ;
Dughera, Stefano .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (03) :430-436
[2]   An Efficient and Scalable Ritter Reaction for the Synthesis of tert-Butyl Amides [J].
Baum, Jean C. ;
Milne, Jacqueline E. ;
Murry, Jerry A. ;
Thiel, Oliver R. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (05) :2207-2209
[3]   Synthesis of amides using the Ritter reaction with bismuth triflate catalysis [J].
Callens, Emmanuel ;
Burton, Andrew J. ;
Barrett, Anthony G. M. .
TETRAHEDRON LETTERS, 2006, 47 (49) :8699-8701
[4]   Asymmetric synthesis of δ-substituted α,β-unsaturated δ-lactams by ring closing metathesis of enantiomerically pure N-acryloyl-homoallylic amines [J].
Fiorelli, Claudio ;
Savoia, Diego .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16) :6022-6028
[5]   An efficient and general iron-catalyzed arylation of benzyl alcohols and benzyl carboxylates [J].
Iovel, I ;
Mertins, K ;
Kischel, J ;
Zapf, A ;
Beller, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (25) :3913-3917
[6]   An efficient FeCl3-catalyzed amidation reaction of secondary benzylic and allylic alcohols with carboxamides or p-toluenesulfonamide [J].
Jana, Umasish ;
Maiti, Sukhendu ;
Biswas, Srijit .
TETRAHEDRON LETTERS, 2008, 49 (05) :858-862
[7]   An FeCl3-catalyzed highly C3-selective Friedel-Crafts alkylation of indoles with alcohols [J].
Jana, Umasish ;
Maiti, Sukhendu ;
Biswas, Srijit .
TETRAHEDRON LETTERS, 2007, 48 (40) :7160-7163
[8]   A simple and efficient FeCl3-catalyzed direct alkylation of active methylene compounds with benzylic and allylic alcohols under mild conditions [J].
Jana, Umasish ;
Biswas, Srijit ;
Maiti, Sukhendu .
TETRAHEDRON LETTERS, 2007, 48 (23) :4065-4069
[9]   Fe3+-montmorillonite K10:: An efficient catalyst for selective amidation of alcohols with nitriles under non-aqueous condition [J].
Lakouraj, MM ;
Movassagh, B ;
Fasihi, J .
SYNTHETIC COMMUNICATIONS, 2000, 30 (05) :821-827
[10]   Convenient removal of N-tert-butyl from amides with scandium triflate [J].
Mahalingam, AK ;
Wu, XY ;
Alterman, M .
TETRAHEDRON LETTERS, 2006, 47 (18) :3051-3053