Ruthenium-catalysed synthesis of tertiary amines from alcohols

被引:99
作者
Haniti, M. [1 ]
Hamid, S. A. [1 ]
Williams, Jonathan M. J. [1 ]
机构
[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
关键词
D O I
10.1016/j.tetlet.2007.09.134
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Secondary amines have been converted into tertiary amines by reactions with primary alcohols. A catalytic system of [Ru(cymene)Cl-2](2) with dppf has been shown to be effective for this transformation for a range of primary alcohols and secondary amines. The methodology has been applied to the one pot synthesis of Piribedil and other piperazine and morpholine-containing products. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8263 / 8265
页数:3
相关论文
共 17 条
[1]   Borrowing hydrogen: Indirect "Wittig" olerination for the formation of C-C bonds from alcohols [J].
Black, Phillip J. ;
Edwards, Michael G. ;
Williams, Jonathan M. J. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (19) :4367-4378
[2]   Borrowing hydrogen: iridium-catalysed reactions for the formation of C-C bonds from alcohols [J].
Black, PJ ;
Cami-Kobeci, G ;
Edwards, MG ;
Slatford, PA ;
Whittlesey, MK ;
Williams, JMJ .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (01) :116-125
[3]   N-alkylation of phenethylamine and tryptamine [J].
Cami-Kobeci, G ;
Slatford, PA ;
Whittlesey, MK ;
Williams, JMJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (03) :535-537
[4]   Conversion of alcohols into N-alkyl anilines via an indirect aza-Wittig reaction [J].
Cami-Kobeci, G ;
Williams, JMJ .
CHEMICAL COMMUNICATIONS, 2004, (09) :1072-1073
[5]   Cyclopentadienyl RuII complexes as highly efficient catalysts for the N-methylation of alkylamines by methanol [J].
Del Zotto, A ;
Baratta, W ;
Sandri, M ;
Verardo, G ;
Rigo, P .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2004, (03) :524-529
[6]   Parallel synthesis of N-arylpiperazines using polymer-assisted reactions [J].
Duncton, MAJ ;
Roffey, JRA ;
Hamlyn, RJ ;
Adams, DR .
TETRAHEDRON LETTERS, 2006, 47 (15) :2549-2552
[7]   Borrowing hydrogen: a catalytic route to C-C bond formation from alcohols [J].
Edwards, MG ;
Jazzar, RFR ;
Paine, BM ;
Shermer, DJ ;
Whittlesey, MK ;
Williams, JMJ ;
Edney, DD .
CHEMICAL COMMUNICATIONS, 2004, (01) :90-91
[8]   N-Alkylation of amines with alcohols catalyzed by a Cp*Ir complex [J].
Fujita, K ;
Li, ZZ ;
Ozeki, N ;
Yamaguchi, R .
TETRAHEDRON LETTERS, 2003, 44 (13) :2687-2690
[9]   TRANSITION METAL-CATALYZED N-ALKYLATION OF AMINES BY ALCOHOLS [J].
GRIGG, R ;
MITCHELL, TRB ;
SUTTHIVAIYAKIT, S ;
TONGPENYAI, N .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (12) :611-612
[10]   Alcohols as electrophiles in C-C bond-forming reactions:: The hydrogen autotransfer process [J].
Guillena, Gabriela ;
Ramon, Diego J. ;
Yus, Miguel .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (14) :2358-2364