Highly efficient iodine-catalyzed hydroarylation of arenes with styrenes

被引：57

作者：

Chu, Cheng-Ming ^{[1
]}

Huang, Wan-Ju ^{[1
]}

Liu, Ju-Tsung ^{[1
]}

Yao, Ching-Fa ^{[1
]}

机构：

[1] Natl Taiwan Normal Univ, Dept Chem, Taipei 116, Taiwan

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 39期

关键词：

Friedel-Crafts reaction; iodine; heteroarenes; hydroarylation; styrene;

D O I：

10.1016/j.tetlet.2007.07.178

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Iodine mediates the hydroarylation of styrenes with arenes and heteroarenes to afford 1,1-diarylalkanes in good to high yields. Details regarding the substrate scope and selectivity of this hydroarylation reaction are discussed. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：6881 / 6885

页数：5

共 68 条

[1] Synthesis of a tricyclic mescaline analogue by catalytic C-H bond activation [J].

Ahrendt, KA ;

Bergman, RG ;

Ellman, JA .

ORGANIC LETTERS, 2003, 5 (08) :1301-1303

[2] New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction [J].

Bandini, M ;

Melloni, A ;

Umani-Ronchi, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (05) :550-556

[3] Iodine-catalyzed highly efficient Michael reaction of indoles under solvent-free condition [J].

Banik, BK ;

Fernandez, M ;

Alvarez, C .

TETRAHEDRON LETTERS, 2005, 46 (14) :2479-2482

[4] Anti-markovnikov hydroarylation of unactivated olefins catalyzed by a bis-tropolonato iridium(III) organometallic complex [J].

Bhalla, G ;

Oxgaard, J ;

Goddard, WA ;

Periana, RA .

ORGANOMETALLICS, 2005, 24 (13) :3229-3232

[5] An efficient, high yield protocol for the one-pot synthesis of dihydropyrimidin-2(1H)-ones catalyzed by iodine [J].

Bhosale, RS ;

Bhosale, SV ;

Wang, TY ;

Zubaidha, PK .

TETRAHEDRON LETTERS, 2004, 45 (49) :9111-9113

[6] Cooperative Friedel-Crafts catalysis in heterobimetallic regime:: Alkylation of aromatics by π-activated alcohols [J].

Choudhury, J ;

Podder, S ;

Roy, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (17) :6162-6163

[7] Iodine-catalyzed Michael addition of mercaptans to α,β-unsaturated ketones under solvent-free conditions [J].

Chu, CM ;

Gao, SJ ;

Sastry, MNV ;

Yao, CF .

TETRAHEDRON LETTERS, 2005, 46 (30) :4971-4974

[8] Efficient, selective deprotection of aromatic acetates catalyzed by Amberlyst-15 or iodine [J].

Das, B ;

Banerjee, J ;

Ramu, R ;

Pal, R ;

Ravindranath, N ;

Ramesh, C .

TETRAHEDRON LETTERS, 2003, 44 (29) :5465-5468

[9] An expedient stereoselective synthesis of (Z)- and (E)-ally iodides from Baylis-Hillman adducts along with selective iodination of benzylic alcohols using the polymethylhydrosiloxane-iodine system [J].

Das, Biswanath ;

Holla, Harish ;

Srinivas, Yallamalla ;

Chowdhury, Nikhil ;

Bandgar, B. P. .

TETRAHEDRON LETTERS, 2007, 48 (18) :3201-3204

[10] Studies on novel synthetic methodologies.: Part 126.: Iodine-catalyzed efficient conjugate addition of pyrroles to α,β-unsaturated ketones [J].

Das, Biswanath ;

Chowdhury, Nikhil ;

Damodar, Kongara .

TETRAHEDRON LETTERS, 2007, 48 (16) :2867-2870

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