Palladium catalysed regioselective arylation of electron-rich olefins by aryl halides

被引：18

作者：

Xu, LJ ^{[1
]}

Chen, WP ^{[1
]}

Xiao, JL ^{[1
]}

机构：

[1] Univ Liverpool, Dept Chem, Leverhulme Ctr Innovat Catalysis, Liverpool L69 7ZD, Merseyside, England

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2002年 / 187卷 / 02期

基金：

英国工程与自然科学研究理事会;

关键词：

palladium; Heck reaction; electron-rich olefins; halides; regioselectivity;

D O I：

10.1016/S1381-1169(02)00272-8

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Palladium catalysed arylation of the electron rich olefin butyl vinyl ether 1 by aryl halides 2 has been accomplished with DPPP/Pd(OAc)(2), (DPPP = 1,3-bis(diphenylphosphino)propane), thus, obviating the need for expensive, commercially unavailable aryl triflates and toxic inorganic additives. In the presence of three equivalents of DPPP, the reaction proceeds with remarkable regioselectivity, leading almost exclusively to substitution by various aryl groups at the olefinic carbon a to the heteroatom of 1. (C) 2002 Elsevier Science B.V. All rights reserved.

引用

页码：189 / 193

页数：5

共 35 条

[1] Formation of palladium(0) complexes from Pd(OAc)2 and a bidentate phosphine ligand (dppp) and their reactivity in oxidative addition [J].

Amatore, C ;

Jutand, A ;

Thuilliez, A .

ORGANOMETALLICS, 2001, 20 (15) :3241-3249

[2] PALLADIUM-CATALYZED BETA-ARYLATION OF MODIFIED VINYL ETHERS WITH ARYL TRIFLATES [J].

BADONE, D ;

GUZZI, U .

TETRAHEDRON LETTERS, 1993, 34 (22) :3603-3606

[3] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

[4]

Brase S, 1998, METAL-CATALYZED CROSS-COUPLING REACTIONS, P99

[5]

BUCKINGHAM J, 1982, DICT ORGANIC COMPOUN

[6] ALPHA-REGIOSELECTIVITY IN PALLADIUM-CATALYZED ARYLATION OF ACYCLIC ENOL ETHERS [J].

CABRI, W ;

CANDIANI, I ;

BEDESCHI, A ;

PENCO, S ;

SANTI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) :1481-1486

[7] PALLADIUM-CATALYZED ARYLATION OF UNSYMMETRICAL OLEFINS - BIDENTATE PHOSPHINE LIGAND CONTROLLED REGIOSELECTIVITY [J].

CABRI, W ;

CANDIANI, I ;

BEDESCHI, A ;

SANTI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) :3558-3563

[8] RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION [J].

CABRI, W ;

CANDIANI, I .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) :2-7

[9] PALLADIUM-CATALYZED REDUCTION OF ARYL SULFONATES - REDUCTION VERSUS HYDROLYSIS AND SELECTIVITY CONTROL [J].

CABRI, W ;

DEBERNARDINIS, S ;

FRANCALANCI, F ;

PENCO, S ;

SANTI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :350-353

[10] 1,10-PHENANTHROLINE DERIVATIVES - A NEW LIGAND CLASS IN THE HECK REACTION - MECHANISTIC ASPECTS [J].

CABRI, W ;

CANDIANI, I ;

BEDESCHI, A ;

SANTI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) :7421-7426

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