A Highly Para-Selective Copper(II)-Catalyzed Direct Arylation of Aniline and Phenol Derivatives

被引：301

作者：

Ciana, Claire-Lise ^{[1
]}

Phipps, Robert J. ^{[1
]}

Brandt, Jochen R. ^{[1
]}

Meyer, Falco-Magnus ^{[1
]}

Gaunt, Matthew J. ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 02期

基金：

瑞士国家科学基金会;

关键词：

aromatic substitution; C-H arylation; copper; hypervalent iodine; synthetic methods; C-H BOND; CATALYZED DIRECT ARYLATION; DIARYLIODONIUM SALTS; UNACTIVATED ARENES; ARYL HALIDES; ACTIVATION; FUNCTIONALIZATION; TRIFLUOROMETHYLATION; SUBSTITUTION; HETEROARENES;

D O I：

10.1002/anie.201004703

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In short order: A copper-catalyzed Friedel-Crafts-type strategy has been developed for the title reaction. An iterative C-H arylation strategy has also been demonstrated for the functionalization of anilines by sequentially delivering different aromatic groups to the para, ortho, and meta positions (see scheme, Bn=benzyl, Piv=pivaloyl). © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：458 / 462

页数：5

共 55 条

[11]

Beck E.M., 2008, ANGEW CHEM INT EDIT, V120, P3046

[12] Synthesis of rhazinicine by a metal-catalyzed C-H bond functionalization strategy [J].

Beck, Elizabeth M. ;

Hatley, Richard ;

Gaunt, Matthew J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (16) :3004-3007

[13] Mild aerobic oxidative palladium (II) catalyzed C-H bond functionalization: Regioselective and switchable C-H alkenylation and annulation of pyrroles [J].

Beck, EM ;

Grimster, NP ;

Hatley, R ;

Gaunt, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) :2528-2529

[14] Recent advances in the synthesis of (hetero)aryl-substituted heteroarenes via transition metal-catalysed direct (hetero)arylation of heteroarene C-H bonds with aryl halides or pseudohalides, diaryliodonium salts, and potassium aryltrifluoroborates [J].

Bellina, Fabio ;

Rossi, Renzo .

TETRAHEDRON, 2009, 65 (50) :10269-10310

[15] Twofold C-H functionalization:: Palladium-catalyzed ortho arylation of anilides [J].

Brasche, Gordon ;

Garcia-Fortanet, Jorge ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2008, 10 (11) :2207-2210

[16]

Chen X., 2009, ANGEW CHEM, V121, P5196

[17] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].

Chen, Xiao ;

Engle, Keary M. ;

Wang, Dong-Hui ;

Yu, Jin-Quan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115

[18] Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].

Colby, Denise A. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

CHEMICAL REVIEWS, 2010, 110 (02) :624-655

[19] Anilide ortho-arylation by using C-H activation methodology [J].

Daugulis, O ;

Zaitsev, VG .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (26) :4046-4048

[20]

Daugulis O., 2005, Angew. Chem, V117, P4114

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