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

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
DOIs	https://doi.org/10.1016/j.cclet.2024.110231
Publication status	E-pub ahead of print - 14 Jul 2024

User-Defined Keywords

Phosphine
Enyne
Pd catalyst
P-chirality
Asymmetric catalysis

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

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.",

year = "2024",

month = jul,

day = "14",

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

language = "English",

journal = "Chinese Chemical Letters",

issn = "1001-8417",

publisher = "Elsevier",

}

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.

PY - 2024/7/14

Y1 - 2024/7/14

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 - Phosphine

KW - Enyne

KW - Pd catalyst

KW - P-chirality

KW - Asymmetric catalysis

UR - https://www.sciencedirect.com/science/article/pii/S1001841724007502?via%3Dihub

U2 - 10.1016/j.cclet.2024.110231

DO - 10.1016/j.cclet.2024.110231

M3 - Journal article

SN - 1001-8417

JO - Chinese Chemical Letters

JF - Chinese Chemical Letters

M1 - 110231

ER -

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

Abstract

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