Direct Arylation of Arene and N-Heteroarenes with Diaryliodonium Salts without the Use of Transition Metal Catalyst

被引：127

作者：

Wen, Jun ^{[1
]}

Zhang, Ruo-Yi ^{[1
]}

Chen, Shan-Yong ^{[1
]}

Zhang, Ji ^{[1
]}

Yu, Xiao-Qi ^{[1
]}

机构：

[1] Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Sichuan, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 01期

基金：

美国国家科学基金会;

关键词：

ONE-POT SYNTHESIS; MEDIATED DIRECT ARYLATION; UNACTIVATED ARENES; BOND FORMATION; ARYL HALIDES; EFFICIENT; BUTOXIDE; ACTIVATION; CHEMISTRY; PYRROLE;

D O I：

10.1021/jo202150t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and simple transition metal-free direct arylation of arene and N-heteroarenes with diaryliodonium salts has been developed. This cross-coupling reaction is promoted only by base and gives the desired products in moderate to good yields.

引用

页码：766 / 771

页数：6

共 50 条

[1] Efficient aryl-(hetero)aryl coupling by activation of C-Cl and C-F bonds using nickel complexes of air-stable phosphine oxides [J].

Ackermann, L ;

Born, R ;

Spatz, JH ;

Meyer, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (44) :7216-7219

[2] Metal-Free Direct Arylations of Indoles and Pyrroles with Diaryliodonium Salts [J].

Ackermann, Lutz ;

Dell'Acqua, Monica ;

Fenner, Sabine ;

Vicente, Ruben ;

Sandmann, Rene .

ORGANIC LETTERS, 2011, 13 (09) :2358-2360

[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], 2003, TOPICS CURRENT CHEM

[5] Regiospecific one-pot synthesis of diaryliodonium tetrafluoroborates from arylboronic acids and aryl iodides [J].

Bielawski, Marcin ;

Aili, David ;

Olofsson, Berit .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12) :4602-4607

[6] Efficient and general one-pot synthesis of diaryliodonium triflates: Optimization, scope and limitations [J].

Bielawski, Marcin ;

Zhu, Mingzhao ;

Olofsson, Berit .

ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (17-18) :2610-2618

[7] High-yielding one-pot synthesis of diaryliodonium triflates from arenes and iodine or aryl iodides [J].

Bielawski, Marcin ;

Olofsson, Berit .

CHEMICAL COMMUNICATIONS, 2007, (24) :2521-2523

[8] The first example for reactivity umpolung of diaryliodonium salts: Chromium(II)-mediated arylation of aldehydes [J].

Chen, DW ;

Takai, K ;

Ochiai, M .

TETRAHEDRON LETTERS, 1997, 38 (47) :8211-8214

[9] A Highly Para-Selective Copper(II)-Catalyzed Direct Arylation of Aniline and Phenol Derivatives [J].

Ciana, Claire-Lise ;

Phipps, Robert J. ;

Brandt, Jochen R. ;

Meyer, Falco-Magnus ;

Gaunt, Matthew J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (02) :458-462

[10] 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

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