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

Wen Yu Liang; Lei Liu; Qing Zhou; Da Yang; Yong Lu; Ye Liu

doi:10.1016/j.mcat.2018.10.016

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

Wen Yu Liang
, Lei Liu
, Qing Zhou
, Da Yang
, Yong Lu
, Ye Liu^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

Research output: Contribution to journal › Article › peer-review

21 Scopus citations

Abstract

The Pd-catalyzed alkoxycarbonylation of alkenes using water as a promoter has been scarcely reported before. Herein, water instead of Brønsted/Lewis acid was found to effectively improve the catalytic performance of Pd(MeCN)₂Cl₂-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)₂Cl₂-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[sbnd]H active species which was responsible for the efficient alkoxycarbonylation of alkenes. In addition, the ligand effect of Xantphos on this reaction was discussed.

Original language	English
Article number	110221
Journal	Molecular Catalysis
Volume	482
DOIs	https://doi.org/10.1016/j.mcat.2018.10.016
State	Published - Feb 2020

Keywords

Alkoxycarbonylation
In situ FT-IR analysis
Palladium hydride

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@article{44873b761d2446708d7d10bd9e1dfb59,

title = "Pd-catalyzed alkoxycarbonylation of alkenes promoted by H2O free of auxiliary acid additive",

abstract = "The Pd-catalyzed alkoxycarbonylation of alkenes using water as a promoter has been scarcely reported before. Herein, water instead of Br{\o}nsted/Lewis acid was found to effectively improve the catalytic performance of Pd(MeCN)2Cl2-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)2Cl2-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[sbnd]H active species which was responsible for the efficient alkoxycarbonylation of alkenes. In addition, the ligand effect of Xantphos on this reaction was discussed.",

keywords = "Alkoxycarbonylation, In situ FT-IR analysis, Palladium hydride",

author = "Liang, \{Wen Yu\} and Lei Liu and Qing Zhou and Da Yang and Yong Lu and Ye Liu",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier B.V.",

year = "2020",

month = feb,

doi = "10.1016/j.mcat.2018.10.016",

language = "英语",

volume = "482",

journal = "Molecular Catalysis",

issn = "2468-8231",

publisher = "Elsevier B.V.",

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TY - JOUR

T1 - Pd-catalyzed alkoxycarbonylation of alkenes promoted by H2O free of auxiliary acid additive

AU - Liang, Wen Yu

AU - Liu, Lei

AU - Zhou, Qing

AU - Yang, Da

AU - Lu, Yong

AU - Liu, Ye

PY - 2020/2

Y1 - 2020/2

N2 - The Pd-catalyzed alkoxycarbonylation of alkenes using water as a promoter has been scarcely reported before. Herein, water instead of Brønsted/Lewis acid was found to effectively improve the catalytic performance of Pd(MeCN)2Cl2-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)2Cl2-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[sbnd]H active species which was responsible for the efficient alkoxycarbonylation of alkenes. In addition, the ligand effect of Xantphos on this reaction was discussed.

AB - The Pd-catalyzed alkoxycarbonylation of alkenes using water as a promoter has been scarcely reported before. Herein, water instead of Brønsted/Lewis acid was found to effectively improve the catalytic performance of Pd(MeCN)2Cl2-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)2Cl2-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[sbnd]H active species which was responsible for the efficient alkoxycarbonylation of alkenes. In addition, the ligand effect of Xantphos on this reaction was discussed.

KW - Alkoxycarbonylation

KW - In situ FT-IR analysis

KW - Palladium hydride

UR - https://www.scopus.com/pages/publications/85055938243

U2 - 10.1016/j.mcat.2018.10.016

DO - 10.1016/j.mcat.2018.10.016

M3 - 文章

AN - SCOPUS:85055938243

SN - 2468-8231

VL - 482

JO - Molecular Catalysis

JF - Molecular Catalysis

M1 - 110221

ER -

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

Abstract

Keywords

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