Copper(II)-Catalyzed meta-Selective Direct Arylation of α-Aryl Carbonyl Compounds

被引：260

作者：

Duong, Hung A. ^{[1
]}

Gilligan, Ruth E. ^{[1
]}

Cooke, Michael L. ^{[1
]}

Phipps, Robert J. ^{[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：

英国工程与自然科学研究理事会;

关键词：

arylation; C-H functionalization; copper; hypervalent iodine; meta substitution; CATALYZED DIRECT ARYLATION; H BOND ACTIVATION; SIMPLE ARENES; OLEFINATION; LIGANDS; SALTS;

D O I：

10.1002/anie.201004704

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Strong competition: A method for the meta-selective arylation of the highly versatile α-aryl carbonyl motif using diaryliodonium salts is described. In this CuII-catalyzed process the remote carbonyl group is capable of overpowering even strongly para-directing functionalities to form the elusive meta-products (see scheme). Remarkably, the arylation process can also operate under metal-free conditions. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：463 / 466

页数：4

共 43 条

[1] SOME BIOLOGICAL PROPERTIES OF 2-(4-ISOBUTYLPHENYL)-PROPIONIC ACID [J].

ADAMS, SS ;

CLIFFE, EE ;

LESSEL, B ;

NICHOLSON, JS .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1967, 56 (12) :1686-+

[2] Regioselective, directed meta acylation of aromatic compounds [J].

Akai, S ;

Peat, AJ ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (36) :9119-9125

[3] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[4]

[Anonymous], 2010, ANGEW CHEM

[5]

[Anonymous], 2010, Angew. Chem.

[6]

Armstrong D. R., 2006, ANGEW CHEM, V118, P3859

[7] Directed meta-metalation using alkali-metal-mediated zincation [J].

Armstrong, David R. ;

Clegg, William ;

Dale, Sophie H. ;

Hevia, Eva ;

Hogg, Lorna M. ;

Honeyman, Gordon W. ;

Mulvey, Robert E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (23) :3775-3778

[8] COPPER CATALYZED PHENYLATION OF INDOLES BY TRIPHENYLBISMUTH BIS-TRIFLUOROACETATE [J].

BARTON, DHR ;

FINET, JP ;

KHAMSI, J .

TETRAHEDRON LETTERS, 1988, 29 (10) :1115-1118

[9] DIRECTED LITHIATION OF AROMATIC TERTIARY AMIDES - AN EVOLVING SYNTHETIC METHODOLOGY FOR POLYSUBSTITUTED AROMATICS [J].

BEAK, P ;

SNIECKUS, V .

ACCOUNTS OF CHEMICAL RESEARCH, 1982, 15 (10) :306-312

[10]

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

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