Aerobic Coupling of Organophosphonium Salts with Alkenes: Catalyst-Free C(sp3)−C(sp2) Bond Formation

Meng Meng Guo; Gan Qi Qin; Xin Yu Jiang; Hao Xu; Mengtao Ma; Zhi Liang Shen; Xue Qiang Chu

doi:10.1002/adsc.202300259

Aerobic Coupling of Organophosphonium Salts with Alkenes: Catalyst-Free C(sp³)−C(sp²) Bond Formation

Meng Meng Guo, Gan Qi Qin, Xin Yu Jiang, Hao Xu, Mengtao Ma, Zhi Liang Shen, Xue Qiang Chu

School of Chemistry and Moleculai Engineering

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

4 Scopus citations

Abstract

An aerobic coupling of benzhydryl phosphonium salts with simple alkenes for accessing trisubstituted olefins is developed under metal-free, catalyst-free, and additive-free conditions. New C(sp³)−C(sp²) bond is constructed via the C−P and C−H bond functionalization by synergistically using O₂ as a “green” oxidant and DMSO as a promoter. The method also distinguishes itself by its broad substrate scope and synthetic potential. Particularly, the use of 1,3,5-trimethoxybenzene fragment in the resulting products as a carbon-based leaving group for further transformations is proved to be feasible.

Original language	English
Pages (from-to)	1871-1876
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	365
Issue number	11
DOIs	https://doi.org/10.1002/adsc.202300259
State	Published - 13 Jun 2023

Keywords

Aerobic coupling
Alkenes
C(sp)−C(sp) Bond formation
Organophosphonium salts
Transition-metal-free condition

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10.1002/adsc.202300259

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title = "Aerobic Coupling of Organophosphonium Salts with Alkenes: Catalyst-Free C(sp3)−C(sp2) Bond Formation",

abstract = "An aerobic coupling of benzhydryl phosphonium salts with simple alkenes for accessing trisubstituted olefins is developed under metal-free, catalyst-free, and additive-free conditions. New C(sp3)−C(sp2) bond is constructed via the C−P and C−H bond functionalization by synergistically using O2 as a “green” oxidant and DMSO as a promoter. The method also distinguishes itself by its broad substrate scope and synthetic potential. Particularly, the use of 1,3,5-trimethoxybenzene fragment in the resulting products as a carbon-based leaving group for further transformations is proved to be feasible.",

keywords = "Aerobic coupling, Alkenes, C(sp)−C(sp) Bond formation, Organophosphonium salts, Transition-metal-free condition",

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T2 - Catalyst-Free C(sp3)−C(sp2) Bond Formation

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AU - Qin, Gan Qi

AU - Jiang, Xin Yu

AU - Xu, Hao

AU - Ma, Mengtao

AU - Shen, Zhi Liang

AU - Chu, Xue Qiang

PY - 2023/6/13

Y1 - 2023/6/13

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AB - An aerobic coupling of benzhydryl phosphonium salts with simple alkenes for accessing trisubstituted olefins is developed under metal-free, catalyst-free, and additive-free conditions. New C(sp3)−C(sp2) bond is constructed via the C−P and C−H bond functionalization by synergistically using O2 as a “green” oxidant and DMSO as a promoter. The method also distinguishes itself by its broad substrate scope and synthetic potential. Particularly, the use of 1,3,5-trimethoxybenzene fragment in the resulting products as a carbon-based leaving group for further transformations is proved to be feasible.

KW - Aerobic coupling

KW - Alkenes

KW - C(sp)−C(sp) Bond formation

KW - Organophosphonium salts

KW - Transition-metal-free condition

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Aerobic Coupling of Organophosphonium Salts with Alkenes: Catalyst-Free C(sp³)−C(sp²) Bond Formation

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Keywords

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