Synthesis of β-aryl ketones by tetraphosphine/palladium catalysed Heck reactions of 2-or 3-substituted allylic alcohols with aryl bromides

被引：42
作者：
Berthiol, F
Doucet, H [1 ]
Santelli, M
机构：
[1] Fac Sci & Tech St Jerome, Synth Organ Lab, UMR 6180, CNRS, F-13397 Marseille 20, France
[2] Univ Aix Marseille 3, F-13397 Marseille 20, France
来源：
TETRAHEDRON | 2006年 / 62卷 / 18期
关键词：
Heck reaction; Baylis-Hillinan adduct; tedicyp; beta-aryl;
D O I：
10.1016/j.tet.2006.02.061
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Through the use of [PdCl(C3H5)](2)/cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinoi-nethyl)cyclopentane as a catalyst, a range of aryl bromides undergoes Heck reaction using 2- or 3-subtituted allylic alcohols. With these sterically congested alkenes, the selective formation of beta-aryl ketones was observed when appropriate reaction conditions were used. The influence of the functional group on the aryl bromide and of the base on the selectivity is remarkable. With several substrates, much higher selectivities were obtained using NaHCO3 instead of K2CO3 as base. Furthermore, this catalyst can be used at low loading with several substrates. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4372 / 4383
页数：12
相关论文
共 40 条
[1]   Arylation of the Baylis-Hillman adducts [J].
Basavaiah, D ;
Muthukumaran, K .
TETRAHEDRON, 1998, 54 (19) :4943-4948
[2]   Heck reactions of 2-substituted enol ethers with aryl bromides catalysed by a tetraphosphine/palladium complex [J].
Battace, A ;
Zair, T ;
Doucet, H ;
Santelli, M .
TETRAHEDRON LETTERS, 2006, 47 (04) :459-462
[3]   Selective synthesis of (E)-triethyl(2-arylethenyl)silane derivatives by reaction of aryl bromides with triethyl vinylsilane catalysed by a palladium-tetraphosphine complex [J].
Battace, A ;
Zair, T ;
Doucet, H ;
Santelli, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (16) :3790-3802
[4]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[5]   Heck reaction of aryl bromides with pent-4-en-2-ol, 2-phenylpent-4-en-2-ol, or hept-6-en-3-ol catalysed by a palladium-tetraphosphine complex [J].
Berthiol, F ;
Doucet, H ;
Santelli, M .
SYNTHESIS-STUTTGART, 2005, (20) :3589-3602
[6]   Heck reactions of aryl bromides with alk-1-en-3-ol derivatives catalysed by a tetraphosphine/palladium complex [J].
Berthiol, F ;
Doucet, H ;
Santelli, M .
TETRAHEDRON LETTERS, 2004, 45 (29) :5633-5636
[7]  
Berthiol F, 2003, SYNLETT, P841
[8]   Heck reaction of aryl halides with linear or cyclic alkenes catalysed by a tetraphosphine/palladium catalyst [J].
Berthiol, F ;
Doucet, H ;
Santelli, M .
TETRAHEDRON LETTERS, 2003, 44 (06) :1221-1225
[9]   Heck reaction of protected allyl alcohols with aryl bromides catalyzed by a tetraphosphanepalladium complex [J].
Berthiol, F ;
Doucet, H ;
Santelli, M .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (07) :1367-1377
[10]   Heck reaction with heteroaryl halides in the presence of a palladium-tetraphosphine catalyst [J].
Berthiol, F ;
Feuerstein, M ;
Doucet, H ;
Santelli, M .
TETRAHEDRON LETTERS, 2002, 43 (32) :5625-5628
1234