Pd(0)/PR3-Catalyzed Intermolecular Arylation of Sp3 C-H Bonds

被引：266

作者：

Wasa, Masayuki ^{[1
]}

Engle, Keary M. ^{[1
]}

Yu, Jin-Quan ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 29期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

PALLADIUM-CATALYZED ARYLATION; ARYL HALIDES; BORONIC ACIDS; ACTIVATION; AIR;

D O I：

10.1021/ja903573p

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Pd(0)-catalyzed intermolecular arylation of sp(3) C-H bonds has been achieved using PR3/Arl. This protocol can be used to arylate a variety of aliphatic carboxylic acid derivatives, including a number of bioactive drug molecules. The use of fluorinated aryl iodides also allows for the introduction of fluorine into a molecule of interest.

引用

收藏

页码：9886 / +

页数：3

相关论文

共 23 条

[1]

AKITA Y, 1982, HETEROCYCLES, V19, P329

[2] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].

Barder, TE ;

Walker, SD ;

Martinelli, JR ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696

[3] Copper-catalyzed oxidative sp3 C-H bond arylation with aryl boronic acids [J].

Basle, Olivier ;

Li, Chao-Jun .

ORGANIC LETTERS, 2008, 10 (17) :3661-3663

[4] The palladium-catalyzed C-H activation of benzylic gem-dialkyl groups [J].

Baudoin, O ;

Herrbach, A ;

Guéritte, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (46) :5736-5740

[5] Two methods for direct ortho-arylation of benzoic acids [J].

Chiong, Hendrich A. ;

Pham, Quynh-Nhu ;

Daugulis, Olafs .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (32) :9879-9884

[6] PALLADIUM-CATALYZED C-H ACTIVATION OF METHOXY GROUPS - A FACILE SYNTHESIS OF SUBSTITUTED 6H-DIBENZO[B,D]PYRANS [J].

DYKER, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (08) :1023-1025

[7] Pd-catalyzed stereoselective oxidation of methyl groups by inexpensive oxidants under mild conditions: A dual role for carboxylic anhydrides in catalytic C-H bond oxidation [J].

Giri, R ;

Liang, J ;

Lei, JG ;

Li, JJ ;

Wang, DH ;

Chen, X ;

Naggar, IC ;

Guo, CY ;

Foxman, BM ;

Yu, JQ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (45) :7420-7424

[8] Synthesis of 1,2-and 1,3-Dicarboxylic Acids via Pd(II)-Catalyzed Carboxylation of Aryl and Vinyl C-H Bonds [J].

Giri, Ramesh ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (43) :14082-+

[9] Anion-accelerated palladium-catalyzed intramolecular coupling of phenols with aryl halides [J].

Hennings, DD ;

Iwasa, S ;

Rawal, VH .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (01) :2-3

[10] Regioselective arylation of benzanilides with aryl triflates or bromides under palladium catalysis [J].

Kametani, Y ;

Satoh, T ;

Miura, M ;

Nomura, M .

TETRAHEDRON LETTERS, 2000, 41 (15) :2655-2658