Chemoselective dehydrogenative esterification of aldehydes and alcohols with a dimeric rhodium(II) catalyst

被引：80

作者：

Cheng, Junjie ^{[1
]}

Zhu, Meijuan ^{[1
]}

Wang, Chao ^{[1
]}

Li, Junjun ^{[1
]}

Jiang, Xue ^{[1
]}

Wei, Yawen ^{[1
]}

Tang, Weijun ^{[1
]}

Xue, Dong ^{[1
]}

Xiao, Jianliang ^{[1
,2
]}

机构：

[1] Shaanxi Normal Univ, Sch Chem & Chem Engn, Minist Educ, Key Lab Appl Surface & Colloid Chem, Xian 710062, Peoples R China

[2] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England

来源：

CHEMICAL SCIENCE | 2016年 / 7卷 / 07期

基金：

英国工程与自然科学研究理事会; 中国国家自然科学基金;

关键词：

AEROBIC OXIDATIVE ESTERIFICATION; C-H; HYDROGEN-TRANSFER; CARBONYLATION REACTIONS; CORRESPONDING ESTERS; BENZYLIC ALCOHOLS; SUPPORTED GOLD; METHYL-ESTERS; CONVERSION; RUTHENIUM;

D O I：

10.1039/c6sc00145a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Dehydrogenative cross-coupling of aldehydes with alcohols as well as dehydrogentive cross-coupling of primary alcohols to produce esters have been developed using a Rh-terpyridine catalyst. The catalyst demonstrates broad substrate scope and good functional group tolerance, affording esters highly selectively. The high chemoselectivity of the catalyst stems from its preference for dehydrogenation of benzylic alcohols over aliphatic ones. Preliminary mechanistic studies suggest that the active catalyst is a dimeric Rh(II) species, operating via a mechanism involving metal-base-metal cooperativity.

引用

页码：4428 / 4434

页数：7

共 98 条

[1] Hydrosilane and bismuth-accelerated palladium catalyzed aerobic oxidative esterification of benzylic alcohols with air [J].

Bai, Xing-Feng ;

Ye, Fei ;

Zheng, Long-Sheng ;

Lai, Guo-Qiao ;

Xia, Chun-Gu ;

Xu, Li-Wen .

CHEMICAL COMMUNICATIONS, 2012, 48 (68) :8592-8594

[2] Palladium-Catalyzed Carbonylation-A Reaction Come of Age [J].

Barnard, Christopher F. J. .

ORGANOMETALLICS, 2008, 27 (21) :5402-5422

[3] PROGRESS IN HYDROFORMYLATION AND CARBONYLATION [J].

BELLER, M ;

CORNILS, B ;

FROHNING, CD ;

KOHLPAINTNER, CW .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 104 (01) :17-85

[4] CATALYTICALLY REACTIVE (ETA-4-TETRACYCLONE)(CO)2(H)2RU AND RELATED COMPLEXES IN DEHYDROGENATION OF ALCOHOLS TO ESTERS [J].

BLUM, Y ;

SHVO, Y .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 282 (01) :C7-C10

[5] Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds [J].

Brennfuehrer, Anne ;

Neumann, Helfried ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4114-4133

[6] Well-Defined Iron Catalysts for the Acceptor less Reversible Dehydrogenation-Hydrogenation of Alcohols and Ketones [J].

Chakraborty, Sumit ;

Lagaditis, Paraskevi O. ;

Foerster, Moritz ;

Bielinski, Elizabeth A. ;

Hazari, Nilay ;

Holthausen, Max C. ;

Jones, William D. ;

Schneider, Sven .

ACS CATALYSIS, 2014, 4 (11) :3994-4003

[7]

Chifotides H.T., 2005, MULTIPLE BONDS METAL, P465

[8] Dehydrogenation and Related Reactions Catalyzed by Iridium Pincer Complexes [J].

Choi, Jongwook ;

MacArthur, Amy H. Roy ;

Brookhart, Maurice ;

Goldman, Alan S. .

CHEMICAL REVIEWS, 2011, 111 (03) :1761-1779

[9] 2,2′: 6′,2"-terpyridines:: From chemical obscurity to common supramolecular motifs [J].

Constable, Edwin C. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (02) :246-253

[10] Chemical routes for the transformation of biomass into chemicals [J].

Corma, Avelino ;

Iborra, Sara ;

Velty, Alexandra .

CHEMICAL REVIEWS, 2007, 107 (06) :2411-2502

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