Relay catalysis over Pd-catalysts induced by two divergent ligands for cascade bis-alkoxycarbonylation of alkynes

Guang Hui Shi; Yu Fen Xie; Xiao Xin Zhang; Jian Guo Qian; Xiao Li Zhao; Yong Lu; Hai Jing Wang; Ye Liu

doi:10.1016/j.jcat.2024.115543

Relay catalysis over Pd-catalysts induced by two divergent ligands for cascade bis-alkoxycarbonylation of alkynes

Guang Hui Shi
, Yu Fen Xie
, Xiao Xin Zhang
, Jian Guo Qian
, Xiao Li Zhao
, Yong Lu
, Hai Jing Wang^*
, Ye Liu^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

5 Scopus citations

Abstract

The mono-metal relay catalysis is a good strategy for one-pot multi-step cascade process in which the specific catalysis can be switched upon the ligand exchange to match the requirements for each independent reaction but without mutual interference and quenching problem. Herein, the one-pot cascade bis-alkoxycarbonylation of terminal alkynes was achieved by taking advantages of the mono-metallic (Pd) relay catalysis, wherein the two kinds of divergent di-phosphines of L1 and DTBPMB were involved. In this Pd(OAc)₂-L1-DTBPMB system, due to the steric bulkiness of L1 and DTBPMB, the two type of catalysts including Pd(OAc)₂-L1 and Pd(OAc)₂-DTBPMB co-existed independently and compatibly. Pd(OAc)₂-L1 system was only in charge of the first-step carbonylation of alkynes towards the branched α,β-unsaturated esters with gem-positioned double bond. Subsequent, Pd(OAc)₂-DTBPMB system took over the carbonylation of the branched α,β-unsaturated esters to afford the target diesters. It was indicated Pd(OAc)₂-L1 system was an efficient and stable catalyst which could be recycled upon 15 runs for the first-step carbonylation. Anyway, Pd(OAc)₂-DTBPMB system easily underwent deactivation, which degraded the recyclability of the Pd(OAc)₂-L1-DTBPMB coupling system for this cascade bis-alkoxycarbonylation.

Original language	English
Article number	115543
Journal	Journal of Catalysis
Volume	434
DOIs	https://doi.org/10.1016/j.jcat.2024.115543
State	Published - Jun 2024

Keywords

Bis-alkoxycarbonylation
Cascade reaction
Di-phosphines
Palladium catalyst
Relay catalysis

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10.1016/j.jcat.2024.115543

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@article{7e02d70f87ab490587c4818106edbe97,

title = "Relay catalysis over Pd-catalysts induced by two divergent ligands for cascade bis-alkoxycarbonylation of alkynes",

abstract = "The mono-metal relay catalysis is a good strategy for one-pot multi-step cascade process in which the specific catalysis can be switched upon the ligand exchange to match the requirements for each independent reaction but without mutual interference and quenching problem. Herein, the one-pot cascade bis-alkoxycarbonylation of terminal alkynes was achieved by taking advantages of the mono-metallic (Pd) relay catalysis, wherein the two kinds of divergent di-phosphines of L1 and DTBPMB were involved. In this Pd(OAc)2-L1-DTBPMB system, due to the steric bulkiness of L1 and DTBPMB, the two type of catalysts including Pd(OAc)2-L1 and Pd(OAc)2-DTBPMB co-existed independently and compatibly. Pd(OAc)2-L1 system was only in charge of the first-step carbonylation of alkynes towards the branched α,β-unsaturated esters with gem-positioned double bond. Subsequent, Pd(OAc)2-DTBPMB system took over the carbonylation of the branched α,β-unsaturated esters to afford the target diesters. It was indicated Pd(OAc)2-L1 system was an efficient and stable catalyst which could be recycled upon 15 runs for the first-step carbonylation. Anyway, Pd(OAc)2-DTBPMB system easily underwent deactivation, which degraded the recyclability of the Pd(OAc)2-L1-DTBPMB coupling system for this cascade bis-alkoxycarbonylation.",

keywords = "Bis-alkoxycarbonylation, Cascade reaction, Di-phosphines, Palladium catalyst, Relay catalysis",

author = "Shi, \{Guang Hui\} and Xie, \{Yu Fen\} and Zhang, \{Xiao Xin\} and Qian, \{Jian Guo\} and Zhao, \{Xiao Li\} and Yong Lu and Wang, \{Hai Jing\} and Ye Liu",

note = "Publisher Copyright: {\textcopyright} 2024 Elsevier Inc.",

year = "2024",

month = jun,

doi = "10.1016/j.jcat.2024.115543",

language = "英语",

volume = "434",

journal = "Journal of Catalysis",

issn = "0021-9517",

publisher = "Academic Press Inc.",

}

TY - JOUR

T1 - Relay catalysis over Pd-catalysts induced by two divergent ligands for cascade bis-alkoxycarbonylation of alkynes

AU - Shi, Guang Hui

AU - Xie, Yu Fen

AU - Zhang, Xiao Xin

AU - Qian, Jian Guo

AU - Zhao, Xiao Li

AU - Lu, Yong

AU - Wang, Hai Jing

AU - Liu, Ye

PY - 2024/6

Y1 - 2024/6

N2 - The mono-metal relay catalysis is a good strategy for one-pot multi-step cascade process in which the specific catalysis can be switched upon the ligand exchange to match the requirements for each independent reaction but without mutual interference and quenching problem. Herein, the one-pot cascade bis-alkoxycarbonylation of terminal alkynes was achieved by taking advantages of the mono-metallic (Pd) relay catalysis, wherein the two kinds of divergent di-phosphines of L1 and DTBPMB were involved. In this Pd(OAc)2-L1-DTBPMB system, due to the steric bulkiness of L1 and DTBPMB, the two type of catalysts including Pd(OAc)2-L1 and Pd(OAc)2-DTBPMB co-existed independently and compatibly. Pd(OAc)2-L1 system was only in charge of the first-step carbonylation of alkynes towards the branched α,β-unsaturated esters with gem-positioned double bond. Subsequent, Pd(OAc)2-DTBPMB system took over the carbonylation of the branched α,β-unsaturated esters to afford the target diesters. It was indicated Pd(OAc)2-L1 system was an efficient and stable catalyst which could be recycled upon 15 runs for the first-step carbonylation. Anyway, Pd(OAc)2-DTBPMB system easily underwent deactivation, which degraded the recyclability of the Pd(OAc)2-L1-DTBPMB coupling system for this cascade bis-alkoxycarbonylation.

AB - The mono-metal relay catalysis is a good strategy for one-pot multi-step cascade process in which the specific catalysis can be switched upon the ligand exchange to match the requirements for each independent reaction but without mutual interference and quenching problem. Herein, the one-pot cascade bis-alkoxycarbonylation of terminal alkynes was achieved by taking advantages of the mono-metallic (Pd) relay catalysis, wherein the two kinds of divergent di-phosphines of L1 and DTBPMB were involved. In this Pd(OAc)2-L1-DTBPMB system, due to the steric bulkiness of L1 and DTBPMB, the two type of catalysts including Pd(OAc)2-L1 and Pd(OAc)2-DTBPMB co-existed independently and compatibly. Pd(OAc)2-L1 system was only in charge of the first-step carbonylation of alkynes towards the branched α,β-unsaturated esters with gem-positioned double bond. Subsequent, Pd(OAc)2-DTBPMB system took over the carbonylation of the branched α,β-unsaturated esters to afford the target diesters. It was indicated Pd(OAc)2-L1 system was an efficient and stable catalyst which could be recycled upon 15 runs for the first-step carbonylation. Anyway, Pd(OAc)2-DTBPMB system easily underwent deactivation, which degraded the recyclability of the Pd(OAc)2-L1-DTBPMB coupling system for this cascade bis-alkoxycarbonylation.

KW - Bis-alkoxycarbonylation

KW - Cascade reaction

KW - Di-phosphines

KW - Palladium catalyst

KW - Relay catalysis

UR - https://www.scopus.com/pages/publications/85192958627

U2 - 10.1016/j.jcat.2024.115543

DO - 10.1016/j.jcat.2024.115543

M3 - 文章

AN - SCOPUS:85192958627

SN - 0021-9517

VL - 434

JO - Journal of Catalysis

JF - Journal of Catalysis

M1 - 115543

ER -

Relay catalysis over Pd-catalysts induced by two divergent ligands for cascade bis-alkoxycarbonylation of alkynes

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Keywords

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