Merging Photoredox with Palladium Catalysis: Decarboxylative ortho-Acylation of Acetanilides with α-Oxocarboxylic Acids under Mild Reaction Conditions

被引：162

作者：

Zhou, Chao ^{[1
]}

Li, Pinhua ^{[1
]}

Zhu, Xianjin ^{[1
]}

Wang, Lei ^{[1
,2
]}

机构：

[1] Huaibei Normal Univ, Dept Chem, Huaibei 235000, Anhui, Peoples R China

[2] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 24期

基金：

中国国家自然科学基金;

关键词：

VISIBLE-LIGHT PHOTOREDOX; C-H FUNCTIONALIZATION; SINGLE-ELECTRON TRANSMETALATION; BENZOPHENONE RELATED-COMPOUNDS; BOND ACYLATION; DERIVATIVES; ALDEHYDES; QUINOLINE; ANILIDES; GOLD;

D O I：

10.1021/acs.orglett.5b03192

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A room temperature decarboxylative ortho-acylation of acetanilides with a-oxocarboxylic acids has been developed via a novel Eosin Y with Pd dual catalytic system. This dual catalytic reaction shows a broad substrate scope and good functional group tolerance, and an array of ortho-acylacetanilides can be afforded in high yields under mild conditions.

引用

页码：6198 / 6201

页数：4

共 65 条

[1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].

Ackermann, Lutz .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295

[2] Synergistic catalysis: A powerful synthetic strategy for new reaction development [J].

Allen, Anna E. ;

MacMillan, David W. C. .

CHEMICAL SCIENCE, 2012, 3 (03) :633-658

[3] New vistas in quinoline synthesis [J].

Atechian, Sarkis ;

Nock, Nadine ;

Norcross, Roger D. ;

Ratni, Hassen ;

Thomas, Andrew W. ;

Verron, Julien ;

Masciadri, Raffaello .

TETRAHEDRON, 2007, 63 (13) :2811-2823

[4] THE COMBINATORIAL SYNTHESIS AND CHEMICAL AND BIOLOGICAL EVALUATION OF A 1,4-BENZODIAZEPINE LIBRARY [J].

BUNIN, BA ;

PLUNKETT, MJ ;

ELLMAN, JA .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (11) :4708-4712

[5] Palladium(II)-Catalyzed Direct ortho-C-H Acylation of Anilides by Oxidative Cross-Coupling with Aldehydes using tert-Butyl Hydroperoxide as Oxidant [J].

Chan, Chun-Wo ;

Zhou, Zhongyuan ;

Yu, Wing-Yiu .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (16) :2999-3006

[6] THE PREPARATION OF INDAZOLES VIA METAL FREE INTRAMOLECULAR ELECTROPHILIC AMINATION OF 2-AMINOPHENYL KETOXIMES [J].

Counceller, Carla M. ;

Eichman, Chad C. ;

Wray, Brenda C. ;

Welin, Eric R. ;

Stambuli, James P. .

ORGANIC SYNTHESES, 2011, 88 :33-41

[7] Bidentate, Monoanionic Auxiliary-Directed Functionalization of Carbon-Hydrogen Bonds [J].

Daugulis, Olafs ;

Roane, James ;

Tran, Ly Dieu .

ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (04) :1053-1064

[8]

Douglas JJ, 2014, ALDRICHIM ACTA, V47, P15

[9] METHODS FOR DRUG DISCOVERY - DEVELOPMENT OF POTENT, SELECTIVE, ORALLY EFFECTIVE CHOLECYSTOKININ ANTAGONISTS [J].

EVANS, BE ;

RITTLE, KE ;

BOCK, MG ;

DIPARDO, RM ;

FREIDINGER, RM ;

WHITTER, WL ;

LUNDELL, GF ;

VEBER, DF ;

ANDERSON, PS ;

CHANG, RSL ;

LOTTI, VJ ;

CERINO, DJ ;

CHEN, TB ;

KLING, PJ ;

KUNKEL, KA ;

SPRINGER, JP ;

HIRSHFIELD, J .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (12) :2235-2246

[10] C-H Functionalization of Phenols Using Combined Ruthenium and Photoredox Catalysis: In Situ Generation of the Oxidant [J].

Fabry, David C. ;

Ronge, Meria A. ;

Zoller, Jochen ;

Rueping, Magnus .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (09) :2801-2805

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