Asymmetric Hydrophosphinylation of Alkynes: Facile Access to Axially Chiral Styrene‐Phosphines

Baohua Cai; Yuan Cui; Jian Zhou; Yong‐Bin Wang; Limin Yang; Bin Tan; Jun Joelle Wang

doi:10.1002/anie.202215820

Asymmetric Hydrophosphinylation of Alkynes: Facile Access to Axially Chiral Styrene‐Phosphines

Baohua Cai
, Yuan Cui
, Jian Zhou
, Yong‐Bin Wang
, Limin Yang^*
, Bin Tan^*
, Jun Joelle Wang^*

^*Corresponding author for this work

Department of Chemistry

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

80 Citations (Scopus)

Abstract

A Cu/CPA co-catalytic system has been developed for achieving the direct hydrophosphinylation of alkynes with phosphine oxides in delivering novel axially chiral phosphorus-containing alkenes in high yields and excellent enantioselectivities (up to 99 % yield and 99 % ee). DFT calculations were performed to elucidate the reaction pathway and the origin of enantiocontrol. This streamlined and modular methodology establishes a new platform for the design and application of new axially chiral styrene-phosphine ligands.

Original language	English
Article number	e202215820
Number of pages	6
Journal	Angewandte Chemie. International Edition
Volume	62
Issue number	3
Early online date	24 Nov 2022
DOIs	https://doi.org/10.1002/anie.202215820
Publication status	Published - 16 Jan 2023

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

SDG 9 Industry, Innovation, and Infrastructure

User-Defined Keywords

Axial Chirality
Chiral Phosphoric Acid
Copper
Hydrophosphinylation
Phosphine

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10.1002/anie.202215820

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@article{a08740849b574ff1a532b68167bf7b73,

title = "Asymmetric Hydrophosphinylation of Alkynes: Facile Access to Axially Chiral Styrene‐Phosphines",

abstract = "A Cu/CPA co-catalytic system has been developed for achieving the direct hydrophosphinylation of alkynes with phosphine oxides in delivering novel axially chiral phosphorus-containing alkenes in high yields and excellent enantioselectivities (up to 99 \% yield and 99 \% ee). DFT calculations were performed to elucidate the reaction pathway and the origin of enantiocontrol. This streamlined and modular methodology establishes a new platform for the design and application of new axially chiral styrene-phosphine ligands.",

keywords = "Axial Chirality, Chiral Phosphoric Acid, Copper, Hydrophosphinylation, Phosphine",

author = "Baohua Cai and Yuan Cui and Jian Zhou and Yong‐Bin Wang and Limin Yang and Bin Tan and Wang, \{Jun Joelle\}",

note = "Funding Information: This research was supported by CARF (Center for Advanced Research in Finance). Funding Information: We are grateful for financial support from the Research Grants Council of Hong Kong (GRF 12301821), the National Natural Science Foundation of China (NSFC 21971102, NSFC 22231004, NSFC 21825105, NSFC 22271071), Guangdong Provincial Key Laboratory of Catalysis (2020B121201002), Guangdong Innovative Program (2019BT02Y335), Shenzhen Science and Technology Program (KQTD20210811090112004), and Natural Science Foundation of Zhejiang Province (LY20B020010. Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

year = "2023",

month = jan,

day = "16",

doi = "10.1002/anie.202215820",

language = "English",

volume = "62",

journal = "Angewandte Chemie. International Edition",

issn = "1433-7851",

publisher = "John Wiley \& Sons Ltd",

number = "3",

}

TY - JOUR

T1 - Asymmetric Hydrophosphinylation of Alkynes

T2 - Facile Access to Axially Chiral Styrene‐Phosphines

AU - Cai, Baohua

AU - Cui, Yuan

AU - Zhou, Jian

AU - Wang, Yong‐Bin

AU - Yang, Limin

AU - Tan, Bin

AU - Wang, Jun Joelle

N1 - Funding Information: This research was supported by CARF (Center for Advanced Research in Finance). Funding Information: We are grateful for financial support from the Research Grants Council of Hong Kong (GRF 12301821), the National Natural Science Foundation of China (NSFC 21971102, NSFC 22231004, NSFC 21825105, NSFC 22271071), Guangdong Provincial Key Laboratory of Catalysis (2020B121201002), Guangdong Innovative Program (2019BT02Y335), Shenzhen Science and Technology Program (KQTD20210811090112004), and Natural Science Foundation of Zhejiang Province (LY20B020010. Publisher Copyright: © 2022 Wiley-VCH GmbH.

PY - 2023/1/16

Y1 - 2023/1/16

N2 - A Cu/CPA co-catalytic system has been developed for achieving the direct hydrophosphinylation of alkynes with phosphine oxides in delivering novel axially chiral phosphorus-containing alkenes in high yields and excellent enantioselectivities (up to 99 % yield and 99 % ee). DFT calculations were performed to elucidate the reaction pathway and the origin of enantiocontrol. This streamlined and modular methodology establishes a new platform for the design and application of new axially chiral styrene-phosphine ligands.

AB - A Cu/CPA co-catalytic system has been developed for achieving the direct hydrophosphinylation of alkynes with phosphine oxides in delivering novel axially chiral phosphorus-containing alkenes in high yields and excellent enantioselectivities (up to 99 % yield and 99 % ee). DFT calculations were performed to elucidate the reaction pathway and the origin of enantiocontrol. This streamlined and modular methodology establishes a new platform for the design and application of new axially chiral styrene-phosphine ligands.

KW - Axial Chirality

KW - Chiral Phosphoric Acid

KW - Copper

KW - Hydrophosphinylation

KW - Phosphine

UR - https://www.scopus.com/pages/publications/85143820696

U2 - 10.1002/anie.202215820

DO - 10.1002/anie.202215820

M3 - Journal article

SN - 1433-7851

VL - 62

JO - Angewandte Chemie. International Edition

JF - Angewandte Chemie. International Edition

IS - 3

M1 - e202215820

ER -

Asymmetric Hydrophosphinylation of Alkynes: Facile Access to Axially Chiral Styrene‐Phosphines

Abstract

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