Pd-catalyzed enantioselective and regioselective asymmetric hydrophosphorylation and hydrophosphinylation of enynes

Yanxin Jiang; Kwai Wun Cheng; Zhiping Yang; Jun Joelle Wang

doi:10.1016/j.cclet.2024.110231

Pd-catalyzed enantioselective and regioselective asymmetric hydrophosphorylation and hydrophosphinylation of enynes

Yanxin Jiang
, Kwai Wun Cheng
, Zhiping Yang^*
, Jun Joelle Wang^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

27 Citations (Scopus)

Abstract

The chemo-, regio-, and enantio-controlled synthesis of P-chiral phosphines in a general and efficient manner remains a significant synthetic challenge. In this study, a Pd-catalyzed hydrofunctionalization is developed for the highly selective synthesis of P-stereogenic alkenylphosphinates and alkenylphosphine oxides via conjugate addition of enynes. Notably, this methodology is suitable for both phosphine oxide and phosphinate nucleophiles, providing a versatile approach for the construction of diverse P-chiral organophosphosphorus compound.

Original language	English
Article number	110231
Number of pages	9
Journal	Chinese Chemical Letters
Volume	36
Issue number	5
Early online date	14 Jul 2024
DOIs	https://doi.org/10.1016/j.cclet.2024.110231
Publication status	Published - May 2025

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 9 Industry, Innovation, and Infrastructure

User-Defined Keywords

Asymmetric catalysis
Enyne
P-chirality
Pd catalyst
Phosphine

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10.1016/j.cclet.2024.110231

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title = "Pd-catalyzed enantioselective and regioselective asymmetric hydrophosphorylation and hydrophosphinylation of enynes",

abstract = "The chemo-, regio-, and enantio-controlled synthesis of P-chiral phosphines in a general and efficient manner remains a significant synthetic challenge. In this study, a Pd-catalyzed hydrofunctionalization is developed for the highly selective synthesis of P-stereogenic alkenylphosphinates and alkenylphosphine oxides via conjugate addition of enynes. Notably, this methodology is suitable for both phosphine oxide and phosphinate nucleophiles, providing a versatile approach for the construction of diverse P-chiral organophosphosphorus compound.",

keywords = "Asymmetric catalysis, Enyne, P-chirality, Pd catalyst, Phosphine",

author = "Yanxin Jiang and Cheng, \{Kwai Wun\} and Zhiping Yang and Wang, \{Jun Joelle\}",

note = "We gratefully thank the National Natural Science Foundation of China (NSFC, No. 22271241), Research Grants Council of Hong Kong (GRF, No. 12303422), and HKBU KRPS grant for financial support. Dr. Xiaoyong Chang from SUSTech is gratefully acknowledged for X-ray crystallographic analysis. Publisher Copyright: {\textcopyright} 2025",

year = "2025",

month = may,

doi = "10.1016/j.cclet.2024.110231",

language = "English",

volume = "36",

journal = "Chinese Chemical Letters",

issn = "1001-8417",

publisher = "Elsevier B.V.",

number = "5",

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TY - JOUR

T1 - Pd-catalyzed enantioselective and regioselective asymmetric hydrophosphorylation and hydrophosphinylation of enynes

AU - Jiang, Yanxin

AU - Cheng, Kwai Wun

AU - Yang, Zhiping

AU - Wang, Jun Joelle

N1 - We gratefully thank the National Natural Science Foundation of China (NSFC, No. 22271241), Research Grants Council of Hong Kong (GRF, No. 12303422), and HKBU KRPS grant for financial support. Dr. Xiaoyong Chang from SUSTech is gratefully acknowledged for X-ray crystallographic analysis. Publisher Copyright: © 2025

PY - 2025/5

Y1 - 2025/5

N2 - The chemo-, regio-, and enantio-controlled synthesis of P-chiral phosphines in a general and efficient manner remains a significant synthetic challenge. In this study, a Pd-catalyzed hydrofunctionalization is developed for the highly selective synthesis of P-stereogenic alkenylphosphinates and alkenylphosphine oxides via conjugate addition of enynes. Notably, this methodology is suitable for both phosphine oxide and phosphinate nucleophiles, providing a versatile approach for the construction of diverse P-chiral organophosphosphorus compound.

AB - The chemo-, regio-, and enantio-controlled synthesis of P-chiral phosphines in a general and efficient manner remains a significant synthetic challenge. In this study, a Pd-catalyzed hydrofunctionalization is developed for the highly selective synthesis of P-stereogenic alkenylphosphinates and alkenylphosphine oxides via conjugate addition of enynes. Notably, this methodology is suitable for both phosphine oxide and phosphinate nucleophiles, providing a versatile approach for the construction of diverse P-chiral organophosphosphorus compound.

KW - Asymmetric catalysis

KW - Enyne

KW - P-chirality

KW - Pd catalyst

KW - Phosphine

UR - https://www.scopus.com/pages/publications/85206239760

U2 - 10.1016/j.cclet.2024.110231

DO - 10.1016/j.cclet.2024.110231

M3 - Journal article

SN - 1001-8417

VL - 36

JO - Chinese Chemical Letters

JF - Chinese Chemical Letters

IS - 5

M1 - 110231

ER -

Pd-catalyzed enantioselective and regioselective asymmetric hydrophosphorylation and hydrophosphinylation of enynes

Abstract

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