Oxidative cross-coupling of arenes induced by single-electron transfer leading to biaryls by use of organoiodine(III) oxidants

被引：222

作者：

Dohi, Toshifumi ^{[1
]}

Ito, Motoki ^{[1
]}

Morimoto, Koji ^{[1
]}

Wata, Minako ^{[1
]}

Kita, Yasuyuki ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 07期

关键词：

C-C coupling; cross-coupling; hypervalent compounds; iodine; oxidation;

D O I：

10.1002/anie.200704495

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Cross-coupling goes green: The direct oxidative cross-coupling reaction of naphthalenes and other electron-rich arenes with mesitylenes has been achieved in high yields using hypervalent iodine(III) reagents. The key for reaction success is the exclusive generation of cation radical intermediates of naphthalenes and the use of mesitylenes as the reactive and less dimerizable nucleophiles. R = alkyl, aryl, halogen, ester, alkoxy, etc. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

收藏

页码：1301 / 1304

页数：4

相关论文

共 58 条

[11] Metal-free synthesis of sterically crowded biphenyls by direct ar-h substitution in alkyl benzenes [J].

Dichiarante, Valentina ;

Tagnoni, Maurizio ;

Albini, Angelo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (34) :6495-6498

[12] Direct synthesis of bipyrroles using phenyliodine bis(trifluoroacetate) with bromotrimethylsilane [J].

Dohi, T ;

Morimoto, K ;

Maruyama, A ;

Kita, Y .

ORGANIC LETTERS, 2006, 8 (10) :2007-2010

[13] The synthesis of head-to-tail (H-T) dimers of 3-substituted thiophenes by the hypervalent iodine(III)-induced oxidative biaryl coupling reaction [J].

Dohi, T ;

Morimoto, K ;

Kiyono, Y ;

Maruyama, A ;

Tohma, H ;

Kita, Y .

CHEMICAL COMMUNICATIONS, 2005, (23) :2930-2932

[14] Versatile direct dehydrative approach for diaryliodonium(III) salts in fluoroalcohol media [J].

Dohi, Toshifumi ;

Ito, Motoki ;

Morimoto, Koji ;

Minamitsuji, Yutaka ;

Takenaga, Naoko ;

Kita, Yasuyuki .

CHEMICAL COMMUNICATIONS, 2007, (40) :4152-4154

[15] Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].

Hassan, J ;

Sévignon, M ;

Gozzi, C ;

Schulz, E ;

Lemaire, M .

CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469

[16] Catalytic asymmetric coupling of 2-naphthols by chiral tridentate oxovanadium(IV) complexes [J].

Hon, SW ;

Li, CH ;

Kuo, JH ;

Barhate, NB ;

Liu, YH ;

Wang, Y ;

Chen, CT .

ORGANIC LETTERS, 2001, 3 (06) :869-872

[17] HIGHLY SELECTIVE OXIDATIVE CROSS-COUPLING OF SUBSTITUTED 2-NAPHTHOLS - A CONVENIENT APPROACH TO UNSYMMETRICAL 1,1'-BINAPHTHALENE-2,2'-DIOLS [J].

HOVORKA, M ;

GUNTEROVA, J ;

ZAVADA, J .

TETRAHEDRON LETTERS, 1990, 31 (03) :413-416

[18] Highly regioselective catalytic oxidative coupling reactions: Synthetic and mechanistic investigations [J].

Hull, Kami L. ;

Lanni, Erica L. ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (43) :14047-14049

[19] Catalytic and highly regioselective cross-coupling of aromatic C-H substrates [J].

Hull, Karni L. ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (39) :11904-+

[20] Novel method of aromatic coupling between N-aryl methanesulfonamide and thiophene derivatives [J].

Jean, Alexandre ;

Cantat, Jonathan ;

Berard, Didier ;

Bouchu, Denis ;

Canesi, Sylvain .

ORGANIC LETTERS, 2007, 9 (13) :2553-2556

← 1 2 3 4 5 6 →