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
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
[1]   Green Chemistry: Principles and Practice [J].
Anastas, Paul ;
Eghbali, Nicolas .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) :301-312
[2]  
BACKVALL JE, 1981, J ORG CHEM, V46, P3479
[3]   THE CHEMISTRY OF ORGANOBISMUTH REAGENTS .13. LIGAND COUPLING INDUCED BY PD(0) [J].
BARTON, DHR ;
OZBALIK, N ;
RAMESH, M .
TETRAHEDRON, 1988, 44 (18) :5661-5668
[4]   Applications of bismuth(III) compounds in organic synthesis [J].
Bothwell, Jason M. ;
Krabbe, Scott W. ;
Mohan, Ram S. .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (09) :4649-4707
[5]   SYNTHESIS OF DIARYLKETONES THROUGH CARBONYLATIVE COUPLING [J].
BRUNET, JJ ;
CHAUVIN, R .
CHEMICAL SOCIETY REVIEWS, 1995, 24 (02) :89-95
[6]   KETONE SYNTHESIS VIA PALLADIUM-CATALYZED CARBONYLATION OF ORGANOALUMINUM COMPOUNDS [J].
BUMAGIN, NA ;
PONOMARYOV, AB ;
BELETSKAYA, IP .
TETRAHEDRON LETTERS, 1985, 26 (39) :4819-4822
[7]   A phosphine-free carbonylative cross-coupling reaction of aryl iodides with arylboronic acids catalyzed by immobilization of palladium in MCM-41 [J].
Cai, Mingzhong ;
Peng, Jian ;
Hao, Wenyan ;
Ding, Guodong .
GREEN CHEMISTRY, 2011, 13 (01) :190-196
[8]   The first heterogeneous carbonylative Stille coupling of organostannanes with aryl iodides catalyzed by MCM-41-supported bidentate phosphine palladium(0) complex [J].
Cai, Mingzhong ;
Zheng, Guomin ;
Ding, Guodong .
GREEN CHEMISTRY, 2009, 11 (10) :1687-1693
[9]   Carbonylative Suzuki-Miyaura Coupling of Arylboronic Acids with Aryl Iodides Catalyzed by the MCM-41-Supported Bidentate Phosphane Palladium(II) Complex [J].
Cai, Mingzhong ;
Zheng, Guomin ;
Zha, Lingfang ;
Peng, Jian .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (10) :1585-1591
[10]   Effect of ligands and additives on the palladium-promoted carbonylative coupling of vinyl stannanes and electron-poor enol triflates [J].
Ceccarelli, S ;
Piarulli, U ;
Gennari, C .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :6254-6256