Phosphine-Free, Heterogeneous Palladium-Catalyzed Atom-Efficient Carbonylative Cross-Coupling of Triarylbismuths with Aryl Iodides: Synthesis of Biaryl Ketones

被引：56

作者：

Hao, Wenyan

Liu, Haiyi

Yin, Lin

Cai, Mingzhong ^{[1
]}

机构：

[1] Jiangxi Normal Univ, Minist Educ, Key Lab Funct Small Organ Mol, Nanchang 330022, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 10期

基金：

中国国家自然科学基金;

关键词：

FRIEDEL-CRAFTS ACYLATION; ONE-POT SYNTHESIS; ARYLBORONIC ACIDS; ACYL CHLORIDES; CARBOXYLIC-ACIDS; BOND FORMATION; IONIC LIQUIDS; HALIDES; CHEMISTRY; ARYLATION;

D O I：

10.1021/acs.joc.6b00570

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and highly efficient heterogeneous palladium-catalyzed carbonylative cross-coupling of aryl iodides with triarylbismuths has been developed that proceeds smoothly at atmospheric CO pressure and provides a general and powerful tool for the preparation of various valuable biaryl ketones with high atom economy, good to excellent yield, and recyclability of the catalyst. The reaction is the first example of Pd-catalyzed carbonylative cross-coupling for the construction of biaryl ketones using triarylbismuths as substrates.

引用

收藏

页码：4244 / 4251

页数：8

相关论文

共 84 条

[51] Palladium(II)-catalyzed aryl coupling of triarylbismuthines under air [J].

Ohe, T ;

Tanaka, T ;

Kuroda, M ;

Cho, CS ;

Ohe, K ;

Uemura, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1999, 72 (08) :1851-1855

[52] SUCCESSFUL APPLICATION OF INDIRECT ELECTROOXIDATION FOR THE TRANSFORMATION OF BIARYL METHANOLS TO THE CORRESPONDING BIARYL KETONES [J].

Okimoto, Mitsuhiro ;

Yoshida, Takashi ;

Hoshi, Masayuki ;

Chiba, Tomohito ;

Maeo, Kei .

SYNTHETIC COMMUNICATIONS, 2011, 41 (21) :3134-3139

[53] Aligned carbon nanotube/polymer composite films with robust flexibility, high transparency, and excellent conductivity [J].

Peng, Huisheng .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (01) :42-+

[54] Atom-efficient metal-catalyzed cross-coupling reaction of indium organometallics with organic electrophiles [J].

Pérez, I ;

Sestelo, JP ;

Sarandeses, LA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) :4155-4160

[55] Antineoplastic agents. 379. Synthesis of phenstatin phosphate [J].

Pettit, GR ;

Toki, B ;

Herald, DL ;

Verdier-Pinard, P ;

Boyd, MR ;

Hamel, E ;

Pettit, RK .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (10) :1688-1695

[56] An in-Ketocyclophane [J].

Qin, Qian ;

Mague, Joel T. ;

Pascal, Robert A., Jr. .

ORGANIC LETTERS, 2010, 12 (05) :928-930

[57] Atom-efficient cross-coupling reactions of triarylbismuths with acyl chlorides under Pd(0) catalysis [J].

Rao, Maddah L. N. ;

Venkatesh, Varadhachari ;

Banerjee, Debasis .

TETRAHEDRON, 2007, 63 (52) :12917-12926

[58] Palladium catalyzed atom-efficient cross-coupling reactions of triarylbismuths with aryl iodides and aryl triflates [J].

Rao, Maddali L. N. ;

Banerjee, Debasis ;

Jadhav, Deepak N. .

TETRAHEDRON LETTERS, 2007, 48 (38) :6644-6647

[59] Synthesis of Functionalized 2-Arylthiophenes with Triarylbismuths as Atom-Efficient Multicoupling Organometallic Nucleophiles under Palladium Catalysis [J].

Rao, Maddali L. N. ;

Banerjee, Debasis ;

Dhanorkar, Ritesh J. .

SYNLETT, 2011, (09) :1324-1330

[60] Palladium-catalyzed cross-coupling reaction of triarylbismuths with aryl halides and triflates [J].

Rao, MLN ;

Yamazaki, O ;

Shimada, S ;

Tanaka, T ;

Suzuki, Y ;

Tanaka, M .

ORGANIC LETTERS, 2001, 3 (25) :4103-4105

← 1 2 3 4 5 6 7 8 9 →