Sulfonate(SO3-)-built-in phosphines for Pd-catalyzed aminocarbonylation/hydroxycarbonylation of alkynes under acid-additive free condition

Long Gen Hu; Guo Sheng Zhang; Guang Hui Shi; Jian Guo Qian; Hai Jing Wang; Ye Liu

doi:10.1016/j.mcat.2025.115321

Sulfonate(SO₃^-)-built-in phosphines for Pd-catalyzed aminocarbonylation/hydroxycarbonylation of alkynes under acid-additive free condition

Long Gen Hu
, Guo Sheng Zhang
, Guang Hui Shi
, Jian Guo Qian
, Hai Jing Wang^*
, Ye Liu

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

Abstract

The Pd-catalyzed aminocarbonylation as well as hydroxycarbonylation of terminal alkynes was achieved with aid of a sulfonate-built-in zwitterionic phosphine (L2), under acid-additive free condition. With L2-Pd(OAc)₂ catalytic system, the terminal alkynes smoothly converted to the corresponding α,β-unsaturated carbonyl compounds (amides or carboxylic acids) in moderate to excellent isolated yields, with 100 % branched regio-selectivity. It was believed that L2 with the matched steric-demand and the bulit-in-SO₃^--unit not only tuned the catalytic performance of Pd(OAc)₂ to activate CO and alkyne but also exhibited the synergetic activating ability towards the nucleophiles of (primary/secondary) amines or H₂O via developing hydrogen-bond interaction, which facilitated the observed successful carbonylation. It means the developed L2-Pd(OAc)₂ system could serve as a bifunctional catalyst.

Original language	English
Article number	115321
Journal	Molecular Catalysis
Volume	585
DOIs	https://doi.org/10.1016/j.mcat.2025.115321
State	Published - Oct 2025

Keywords

Aminocarbonylation
Bifunctional catalyst
Hydroxycarbonylation
Sulfonate-built-in-phosphine
Zwitterionic ligand

Access to Document

10.1016/j.mcat.2025.115321

Cite this

@article{d00643ea487b4ecda032a6a0312ebdce,

title = "Sulfonate(SO3-)-built-in phosphines for Pd-catalyzed aminocarbonylation/hydroxycarbonylation of alkynes under acid-additive free condition",

abstract = "The Pd-catalyzed aminocarbonylation as well as hydroxycarbonylation of terminal alkynes was achieved with aid of a sulfonate-built-in zwitterionic phosphine (L2), under acid-additive free condition. With L2-Pd(OAc)2 catalytic system, the terminal alkynes smoothly converted to the corresponding α,β-unsaturated carbonyl compounds (amides or carboxylic acids) in moderate to excellent isolated yields, with 100 \% branched regio-selectivity. It was believed that L2 with the matched steric-demand and the bulit-in-SO3--unit not only tuned the catalytic performance of Pd(OAc)2 to activate CO and alkyne but also exhibited the synergetic activating ability towards the nucleophiles of (primary/secondary) amines or H2O via developing hydrogen-bond interaction, which facilitated the observed successful carbonylation. It means the developed L2-Pd(OAc)2 system could serve as a bifunctional catalyst.",

keywords = "Aminocarbonylation, Bifunctional catalyst, Hydroxycarbonylation, Sulfonate-built-in-phosphine, Zwitterionic ligand",

author = "Hu, \{Long Gen\} and Zhang, \{Guo Sheng\} and Shi, \{Guang Hui\} and Qian, \{Jian Guo\} and Wang, \{Hai Jing\} and Ye Liu",

note = "Publisher Copyright: {\textcopyright} 2025 Elsevier B.V.",

year = "2025",

month = oct,

doi = "10.1016/j.mcat.2025.115321",

language = "英语",

volume = "585",

journal = "Molecular Catalysis",

issn = "2468-8231",

publisher = "Elsevier B.V.",

}

TY - JOUR

T1 - Sulfonate(SO3-)-built-in phosphines for Pd-catalyzed aminocarbonylation/hydroxycarbonylation of alkynes under acid-additive free condition

AU - Hu, Long Gen

AU - Zhang, Guo Sheng

AU - Shi, Guang Hui

AU - Qian, Jian Guo

AU - Wang, Hai Jing

AU - Liu, Ye

PY - 2025/10

Y1 - 2025/10

N2 - The Pd-catalyzed aminocarbonylation as well as hydroxycarbonylation of terminal alkynes was achieved with aid of a sulfonate-built-in zwitterionic phosphine (L2), under acid-additive free condition. With L2-Pd(OAc)2 catalytic system, the terminal alkynes smoothly converted to the corresponding α,β-unsaturated carbonyl compounds (amides or carboxylic acids) in moderate to excellent isolated yields, with 100 % branched regio-selectivity. It was believed that L2 with the matched steric-demand and the bulit-in-SO3--unit not only tuned the catalytic performance of Pd(OAc)2 to activate CO and alkyne but also exhibited the synergetic activating ability towards the nucleophiles of (primary/secondary) amines or H2O via developing hydrogen-bond interaction, which facilitated the observed successful carbonylation. It means the developed L2-Pd(OAc)2 system could serve as a bifunctional catalyst.

AB - The Pd-catalyzed aminocarbonylation as well as hydroxycarbonylation of terminal alkynes was achieved with aid of a sulfonate-built-in zwitterionic phosphine (L2), under acid-additive free condition. With L2-Pd(OAc)2 catalytic system, the terminal alkynes smoothly converted to the corresponding α,β-unsaturated carbonyl compounds (amides or carboxylic acids) in moderate to excellent isolated yields, with 100 % branched regio-selectivity. It was believed that L2 with the matched steric-demand and the bulit-in-SO3--unit not only tuned the catalytic performance of Pd(OAc)2 to activate CO and alkyne but also exhibited the synergetic activating ability towards the nucleophiles of (primary/secondary) amines or H2O via developing hydrogen-bond interaction, which facilitated the observed successful carbonylation. It means the developed L2-Pd(OAc)2 system could serve as a bifunctional catalyst.

KW - Aminocarbonylation

KW - Bifunctional catalyst

KW - Hydroxycarbonylation

KW - Sulfonate-built-in-phosphine

KW - Zwitterionic ligand

UR - https://www.scopus.com/pages/publications/105010517444

U2 - 10.1016/j.mcat.2025.115321

DO - 10.1016/j.mcat.2025.115321

M3 - 文章

AN - SCOPUS:105010517444

SN - 2468-8231

VL - 585

JO - Molecular Catalysis

JF - Molecular Catalysis

M1 - 115321

ER -

Sulfonate(SO₃^-)-built-in phosphines for Pd-catalyzed aminocarbonylation/hydroxycarbonylation of alkynes under acid-additive free condition

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this