Intramolecular metathesis versus Kharasch reactions using the Grubbs metathesis catalyst: towards catalyst economy

被引:35
作者
Faulkner, J
Edlin, CD
Fengas, D
Preece, I
Quayle, P [1 ]
Richards, SN
机构
[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
[2] Avecia, Manchester M9 8ZS, Lancs, England
[3] GlaxoSmithKline, Med Res Ctr, Stevenage SG1 2NY, Herts, England
基金
英国工程与自然科学研究理事会;
关键词
Grubbs; metathesis; Kharasch; cyclisation; competition; decomposition; stability; ATRC; RCM;
D O I
10.1016/j.tetlet.2005.02.060
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first generation Grubbs catalyst can promote either ring closing metathesis (RCM) or atom transfer radical cyclisation reactions (ATRC) depending upon the reaction conditions employed. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2381 / 2385
页数:5
相关论文
共 24 条
[1]   Two birds with one metallic stone: Single-pot catalysis of fundamentally different transformations [J].
Ajamian, A ;
Gleason, JL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) :3754-3760
[2]   Non-metathetic behavior patterns of Grubbs' carbene [J].
Alcaide, B ;
Almendros, P .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (06) :1259-1262
[3]   Regio- and stereoselective hydrosilylation of terminal alkynes using Grubbs' first-generation olefin-metathesis catalyst [J].
Aricó, CS ;
Cox, LR .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (18) :2558-2562
[4]   Tandem catalysis: Three mechanistically distinct reactions from a single ruthenium complex [J].
Bielawski, CW ;
Louie, J ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) :12872-12873
[5]   One-pot, one-catalyst synthesis of graft copolymers by controlled ROMP and ATRP polymerizations [J].
Charvet, R ;
Novak, BM .
MACROMOLECULES, 2004, 37 (23) :8808-8811
[6]   Atom transfer radical cyclisations of activated and unactivated N-allylhaloacetamides and N-homoallylhaloacetamides using chiral and non-chiral copper complexes [J].
Clark, AJ ;
De Campo, F ;
Deeth, RJ ;
Filik, RP ;
Gatard, S ;
Hunt, NA ;
Lastécouères, D ;
Thomas, GH ;
Verlhac, JB ;
Wongtap, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (05) :671-680
[7]  
EDLIN CD, 2005, IN PRESS SYNLETT
[8]  
FENGAS D, UNPUB
[9]   Olefin metathesis [J].
Grubbs, RH .
TETRAHEDRON, 2004, 60 (34) :7117-7140
[10]   Decomposition of a key intermediate in ruthenium-catalyzed olefin metathesis reactions [J].
Hong, SH ;
Day, MW ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7414-7415