Bifunctional ligands for Pd-catalyzed selective alkoxycarbonylation of alkynes

被引:30
作者
Qi, Huimin [1 ,2 ]
Huang, Zijun [1 ]
Wang, Menglan [1 ]
Yang, Peiju [1 ]
Du, Chen-Xia [3 ]
Chen, Shu-Wei [2 ]
Li, Yuehui [1 ]
机构
[1] Chinese Acad Sci, LICP, Ctr Excellence Mol Synth, Suzhou Res Inst LICP,State Key Lab Oxo Synth & Se, Lanzhou 730000, Gansu, Peoples R China
[2] Northwest A&F Univ, Coll Chem & Pharm, Yangling 712100, Shaanxi, Peoples R China
[3] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Henan, Peoples R China
关键词
Carbonylation; Alkyne; Palladium; Bifunctional ligand; Unsaturated ester; PAUSON-KHAND REACTION; PALLADIUM CATALYST; UNSATURATED ESTERS; CARBONYLATION; METHOXYCARBONYLATION; ACETYLENE; ALKENES; HYDROFORMYLATION; MECHANISM; OLEFINS;
D O I
10.1016/j.jcat.2018.04.007
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Catalytic carbonylations of alkynes represent straightforward and atom-economic synthesis of a, beta-unsaturated carbonyl compounds. One of the issues associated with the currently known catalytic systems is insufficient efficiency. In this context, Pd/ligand-catalyzed regioselective and efficient alkoxycarbonylation of terminal alkynes is desirable for the synthesis of alpha,beta-unsaturated esters. Herein, we present the use of a newly designed bifunctional ligand for efficient Pd-catalyzed alkoxycarbonylation of alkynes. Both aliphatic and aromatic alkynes were smoothly transformed to the branched desired products with high selectivity (28 examples, 45-96% yields, 95.0-99.9% selectivity). (C) 2018 Elsevier Inc. All rights reserved.
引用
收藏
页码:63 / 68
页数:6
相关论文
共 39 条
[1]   A SIMPLE AND MILD METHOD FOR THE DIRECT METAL-CATALYZED CARBONYLATION OF ALLYL ALCOHOLS TO ACIDS [J].
ALPER, H ;
AMER, I .
JOURNAL OF MOLECULAR CATALYSIS, 1989, 54 (02) :L33-L36
[2]   Alkaline Earth-Centered CO Homologation, Reduction, and Amine Carbonylation [J].
Anker, Mathew D. ;
Kefalidis, Christos E. ;
Yang, Yan ;
Fang, Jian ;
Hill, Michael S. ;
Mahon, Mary F. ;
Maron, Laurent .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (29) :10036-10054
[3]  
Beller M, 2006, TOP ORGANOMETAL CHEM, V18, P1, DOI 10.1007/b105253
[4]  
Boddien A., 2012, ORGANIC CHEM BREAKTH, P683
[5]  
Borner A., 2016, HYDROFORMYLATION FUN
[6]   DFT computational study of the mechanism of allyl halides carbonylation catalyzed by nickel tetracarbonyl [J].
Bottoni, A ;
Miscione, GP ;
Novoa, JJ ;
Prat-Resina, X .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) :10412-10419
[7]   Transition-metal-catalyzed transfer carbonylation with HCOOH or HCHO as non-gaseous C1 source [J].
Cao, Jian ;
Zheng, Zhan-Jiang ;
Xu, Zheng ;
Xu, Li-Wen .
COORDINATION CHEMISTRY REVIEWS, 2017, 336 :43-53
[8]   Asymmetric approach to (+)-beta-cuparenone by intramolecular Pauson-Khand reaction [J].
Castro, J ;
Moyano, A ;
Pericas, MA ;
Riera, A ;
Greene, AE ;
AlvarezLarena, A ;
Piniella, JF .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) :9016-9020
[9]   Cu-Catalyzed Hydrocarbonylative C-C Coupling of Terminal Alkynes with Alkyl Iodides [J].
Cheng, Li-Jie ;
Mankad, Neal P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (30) :10200-10203
[10]   Mechanism of Alkyne Alkoxycarbonylation at a Pd Catalyst with P,N Hemilabile Ligands: A Density Functional Study [J].
Crawford, Luke ;
Cole-Hamilton, David J. ;
Drent, Eite ;
Buehl, Michael .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (43) :13923-13926