Pd-catalyzed alkoxycarbonylation of alkenes promoted by H2O free of auxiliary acid additive

被引:15
作者
Liang, Wen-Yu [1 ]
Liu, Lei [1 ]
Zhou, Qing [1 ]
Yang, Da [1 ]
Lu, Yong [1 ]
Liu, Ye [1 ]
机构
[1] East China Normal Univ, Sch Chem & Mol Engn, Shanghai Key Lab Green Chem & Chem Proc, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China
基金
中国国家自然科学基金;
关键词
Alkoxycarbonylation; Palladium hydride; In situ FT-IR analysis; PALLADIUM COMPLEXES; DIRECT CARBONYLATION; METHOXYCARBONYLATION; LIGANDS; HYDROESTERIFICATION; STYRENE; EFFICIENT; DIPHOSPHINES; MECHANISM; OLEFINS;
D O I
10.1016/j.mcat.2018.10.016
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
The Pd-catalyzed alkoxycarbonylation of alkenes using water as a promoter has been scarcely reported before. Herein, water instead of Bronsted/Lewis acid was found to effectively improve the catalytic performance of Pd (MeCN)(2)Cl-2-Xantphos system for alkoxycarbonylation of alkenes. Under the optimal conditions, the best yield of 97% was obtained for the target products (methyl 3-phenylpropanoate and methyl 2-phenylpropanoate) with L/B of 4.3 and TON of 192. With the involvement of water, Pd(MeCN)(2)Cl-2-Xantphos system also exhibited the moderate to good generality to alkoxycarbonylation of different kinds of alkenes with alcohols. The in situ high pressure FT-IR analysis verified that water played an important role in promoting formation and stability of Pd-H active species which was responsible for the efficient alkoxycarbonylation of alkenes. In addition, the ligand effect of Xantphos on this reaction was discussed.
引用
收藏
页数:6
相关论文
共 33 条
[1]   Methoxycarbonylation of Styrene Using a New Type of Palladium Complexes Bearing P,N-donor Ligands as Catalysts [J].
Abarca, Gabriel ;
Brown, Kareen ;
Moya, Sergio A. ;
Bayon, J. Carles ;
Aguirre, Pedro A. .
CATALYSIS LETTERS, 2015, 145 (07) :1396-1402
[2]   Pd-Catalyzed Regioselective Alkoxycarbonylation of 1-Alkenes Using a Lewis Acid [SnCl2 or Ti(OiPr)4] and a Phosphine [J].
Amezquita-Valencia, Manuel ;
Achonduh, George ;
Alper, Howard .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (12) :6419-6424
[3]   Ruthenium- and rhodium-catalyzed direct carbonylation of the ortho C-H bond in the benzene ring of N-arylpyrazoles [J].
Asaumi, T ;
Matsuo, T ;
Fukuyama, T ;
Ie, Y ;
Kakiuchi, F ;
Chatani, N .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (13) :4433-4440
[4]   Aluminum triflate as a highly active and efficient nonprotic cocatalyst in the palladium-catalyzed methoxycarbonylation reaction [J].
Bradley, D. ;
Williams, G. ;
Shaw, Megan L. ;
Green, Michael J. ;
Holzapfel, Cedric W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) :560-563
[5]   Characterization and catalytic activity of trans-[Pd(COCH2CH3) (TsO)(PPh3)2], isolated from the hydro-methoxycarbonylation of ethene catalyzed by [Pd(TsO)2(PPh3)2-] [J].
Cavinato, G ;
Toniolo, L ;
Vavasori, A .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 219 (02) :233-240
[6]   Amphiphilic Zwitterionic phosphine based Au(I)-complex as efficient and recyclable catalyst for hydration of alkynes free of additional additives [J].
Chen, Xia ;
Ye, Xu ;
Liang, Wen-Yu ;
Zhou, Qing ;
Giang Vo-Thanh ;
Liu, Ye .
MOLECULAR CATALYSIS, 2018, 448 :171-176
[7]   Chemicals from Alkynes with Palladium Catalysts [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL REVIEWS, 2014, 114 (03) :1783-1826
[8]   Highly active and efficient catalysts for alkoxycarbonylation of alkenes [J].
Dong, Kaiwu ;
Fang, Xianjie ;
Gulak, Samet ;
Franke, Robert ;
Spannenberg, Anke ;
Neumann, Helfried ;
Jackstell, Ralf ;
Beller, Matthias .
NATURE COMMUNICATIONS, 2017, 8
[9]   CHEMISTRY OF METAL-DIENE COMPLEXES - A NEW CONVENIENT SYNTHESIS OF PALLADIUM(II) HYDRIDE COMPLEXES [J].
GOEL, AB ;
GOEL, S .
INORGANICA CHIMICA ACTA-LETTERS, 1980, 45 (03) :L85-L86
[10]   Electronic effect of diphosphines on the regioselectivity of the palladium-catalyzed hydroesterification of styrene [J].
Guiu, Ester ;
Caporali, Maria ;
Munoz, Bianca ;
Muller, Christian ;
Lutz, Martin ;
Spek, Anthony L. ;
Claver, Carmen ;
van Leeuwen, Piet W. N. M. .
ORGANOMETALLICS, 2006, 25 (13) :3102-3104