Protodecarboxylation of benzoic acids under radical conditions

被引：98

作者：

Seo, Sangwon ^{[1
]}

Taylor, John B. ^{[2
]}

Greaney, Michael F. ^{[1
]}

机构：

[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

[2] Syngenta, Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 66期

基金：

英国工程与自然科学研究理事会;

关键词：

COUPLING REACTIONS; CARBOXYLIC-ACIDS; DECARBOXYLATION; ARYLATION; KINETICS;

D O I：

10.1039/c2cc33306f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new approach to protodecarboxylation is described that enhances the substrate scope for benzoic acids. The reaction uses oxidative radical conditions to decarboxylate a variety of acids in acetonitrile.

引用

页码：8270 / 8272

页数：3

共 30 条

[11] PRODUCTS AND KINETICS OF DECARBOXYLATION OF ACTIVATED AND UNACTIVATED AROMATIC CUPROUS CARBOXYLATES IN PYRIDINE AND IN QUINOLINE [J].

COHEN, T ;

BERNINGER, RW ;

WOOD, JT .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (05) :837-848

[12]

Cornella J., 2012, SYNTHESIS-STUTTGART, V44, P1670

[13] Carboxylic Acids as Traceless Directing Groups for Formal meta-Selective Direct Arylation [J].

Cornella, Josep ;

Righi, Marika ;

Larrosa, Igor .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (40) :9429-9432

[14] Silver-catalysed protodecarboxylation of ortho-substituted benzoic acids [J].

Cornella, Josep ;

Sanchez, Carolina ;

Banawa, David ;

Larrosa, Igor .

CHEMICAL COMMUNICATIONS, 2009, (46) :7176-7178

[15] Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds [J].

Daugulis, Olafs ;

Do, Hien-Quang ;

Shabashov, Dmitry .

ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) :1074-1086

[16] Development of a catalytic aromatic decarboxylation reaction [J].

Dickstein, Joshua S. ;

Mulrooney, Carol A. ;

O'Brien, Erin M. ;

Morgan, Barbara J. ;

Kozlowski, Marisa C. .

ORGANIC LETTERS, 2007, 9 (13) :2441-2444

[17] Carboxylates as sources of carbon nucleophiles and electrophiles: comparison of decarboxylative and decarbonylative pathways [J].

Dzik, Wojciech I. ;

Lange, Paul P. ;

Goossen, Lukas J. .

CHEMICAL SCIENCE, 2012, 3 (09) :2671-2678

[18] Copper-catalyzed protodecarboxylation of aromatic carboxylic acids [J].

Goossen, Lukas J. ;

Thiel, Werner R. ;

Rodriguez, Nuria ;

Linder, Christophe ;

Melzer, Bettina .

ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (14-15) :2241-2246

[19] Comparative Study of Copper- and Silver-Catalyzed Protodecarboxylations of Carboxylic Acids [J].

Goossen, Lukas J. ;

Rodriguez, Nuria ;

Linder, Christophe ;

Lange, Paul P. ;

Fromm, Andreas .

CHEMCATCHEM, 2010, 2 (04) :430-442

[20] Silver-catalysed protodecarboxylation of carboxylic acids [J].

Goossen, Lukas J. ;

Linder, Christophe ;

Rodriguez, Nuria ;

Lange, Paul P. ;

Fromm, Andreas .

CHEMICAL COMMUNICATIONS, 2009, (46) :7173-7175

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