Rh(I)-Catalyzed Decarboxylative Transformations of Arenecarboxylic Acids: Ligand- and Reagent-Controlled Selectivity toward Hydrodecarboxylation or Heck-Mizoroki Products

被引：115

作者：

Sun, Zhong-Ming ^{[1
]}

Zhang, Jing ^{[1
]}

Zhao, Pinjing ^{[1
]}

机构：

[1] N Dakota State Univ, Dept Chem & Mol Biol, Fargo, ND 58105 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 05期

基金：

美国国家科学基金会;

关键词：

AROMATIC CARBOXYLIC-ACIDS; CROSS-COUPLING REACTION; CATALYZED PROTODECARBOXYLATION; CONJUGATE ADDITION; BIARYL SYNTHESIS; BENZOIC-ACIDS; ARYL HALIDES; ARENE; OLEFINATION; ESTERS;

D O I：

10.1021/ol100001b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Rh(I)-based catalyst system has been developed to promote three types of decarboxylative transformations of arenecarboxylic acids: (1) hydrodecarboxylation, (2) Heck-Mizoroki olefination, and (3) conjugate addition. Scopes of reactions (1) and (2) were studied, and the ligand and reagent dependence of selectivity was explored.

引用

页码：992 / 995

页数：4

共 38 条

[31] Waste-Free Synthesis of Condensed Heterocyclic Compounds by Rhodium-Catalyzed Oxidative Coupling of Substituted Arene or Heteroarene Carboxylic Acids with Alkynes [J].

Shimizu, Masaki ;

Hirano, Koji ;

Satoh, Tetsuya ;

Miura, Masahiro .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (09) :3478-3483

[32] Rhodium-Mediated Decarboxylative Conjugate Addition of Fluorinated Benzoic Acids: Stoichiometric and Catalytic Transformations [J].

Sun, Zhong-Ming ;

Zhao, Pinjing .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (36) :6726-6730

[33] On the mechanism of the palladium(II)-catalyzed decarboxylative olefination of arene carboxylic acids. Crystallographic characterization of non-phosphine palladium(II) intermediates and observation of their stepwise transformation in Heck-like processes [J].

Tanaka, D ;

Romeril, SP ;

Myers, AG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (29) :10323-10333

[34] Heck-type arylation of 2-cycloalken-1-ones with arylpalladium intermediates formed by decarboxylative palladation and by aryl iodide insertion [J].

Tanaka, D ;

Myers, AG .

ORGANIC LETTERS, 2004, 6 (03) :433-436

[35] Rhodium- and iridium-catalyzed oxidative coupling of benzoic acids with alkynes via regioselective C-H bond cleavage [J].

Ueura, Kenji ;

Satoh, Tetsuya ;

Miura, Masahiro .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14) :5362-5367

[36] Palladium-catalyzed decarboxylative coupling of aromatic acids with aryl halides or unactivated arenes using microwave heating [J].

Voutchkova, Adelina ;

Coplin, Abigail ;

Leadbeater, Nicholas E. ;

Crabtree, Robert H. .

CHEMICAL COMMUNICATIONS, 2008, (47) :6312-6314

[37] Palladium-catalyzed decarboxylative sp3-sp3 coupling of nitrobenzene acetic esters [J].

Waetzig, Shelli R. ;

Tunge, Jon A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (48) :14860-+

[38]

Zou G, 2007, DALTON T, P3055, DOI 10.1039/b615473e

← 1 2 3 4 →