Regioselective Heck arylation of unsaturated alcohols by palladium catalysis in ionic liquid

被引：61

作者：

Mo, Jun ^{[1
]}

Xu, Lijin ^{[1
]}

Ruan, Jiwu ^{[1
]}

Liu, Shifang ^{[1
]}

Xiao, Jianliang ^{[1
]}

机构：

[1] Univ Liverpool, Dept Chem, Liverpool Ctr Mat & Catalysis, Liverpool L69 7ZD, Merseyside, England

来源：

CHEMICAL COMMUNICATIONS | 2006年 / 34期

关键词：

D O I：

10.1039/b608033b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In contrast to almost all of the known examples of Heck arylation of unsaturated alcohols, which yield predominately beta-arylated products, arylation under the Pd-DPPP catalysis in ionic liquid leads preferentially to aryl substitution at the a carbon, providing an easy pathway to this valuable class of olefins.

引用

页码：3591 / 3593

页数：3

共 38 条

[1] Dioxygen-promoted regioselective oxidative Heck arylations of electron-rich olefins with arylboronic acids
Andappan, MMS
Nilsson, P
von Schenck, H
Larhed, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) : 5212 - 5218
[2] The heck reaction as a sharpening stone of palladium catalysis
Beletskaya, IP
Cheprakov, AV
[J]. CHEMICAL REVIEWS, 2000, 100 (08) : 3009 - 3066
[3] Synthesis of β-aryl ketones by tetraphosphine/palladium catalysed Heck reactions of 2-or 3-substituted allylic alcohols with aryl bromides
Berthiol, F
Doucet, H
Santelli, M
[J]. TETRAHEDRON, 2006, 62 (18) : 4372 - 4383
[4] PALLADIUM-CATALYZED ARYLATION OF UNSYMMETRICAL OLEFINS - BIDENTATE PHOSPHINE LIGAND CONTROLLED REGIOSELECTIVITY
CABRI, W
CANDIANI, I
BEDESCHI, A
SANTI, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) : 3558 - 3563
[5] RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION
CABRI, W
CANDIANI, I
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) : 2 - 7
[6] 1,10-PHENANTHROLINE DERIVATIVES - A NEW LIGAND CLASS IN THE HECK REACTION - MECHANISTIC ASPECTS
CABRI, W
CANDIANI, I
BEDESCHI, A
SANTI, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) : 7421 - 7426
[7] PALLADIUM-CATALYZED VINYL SUBSTITUTION-REACTIONS .1. NEW SYNTHESIS OF 2-PHENYL AND 3-PHENYL SUBSTITUTED ALLYLIC ALCOHOLS, ALDEHYDES, AND KETONES FROM ALLYLIC ALCOHOLS
CHALK, AJ
MAGENNIS, SA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (02) : 273 - 278
[8] An efficient, palladium-catalyzed, enantioselective synthesis of (2R)-3-butene-1,2-diol and its use in highly selective Heck reactions
Cheeseman, N
Fox, M
Jackson, M
Lennon, IC
Meek, G
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) : 5396 - 5399
[9] Kinetic study of the addition of trihalides to unsaturated compounds in ionic liquids.: Evidence of a remarkable solvent effect in the reaction of ICl2-
Chiappe, C
Pieraccini, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (18) : 6059 - 6064
[10] Electronic control of the reglochemistry in palladium - Phosphine catalyzed intermolecular heck reactions
Deeth, RJ
Smith, A
Brown, JM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (22) : 7144 - 7151

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