PIII-Chelation-Enabled Ni(0)-Catalyzed Alkenylation of Nonacidic C–H in Biarylphosphines with Alkynes

Abstract A P(III)-chelation-assisted Ni(0)-catalyzed C–H alkenylation of biarylphosphines with alkynes is reported, enabling the functionalization of nonacidic arene C–H bonds without a stoichiometric base. The protocol accommodates a broad range of biarylphosphines and alkynes, affording diversely alkenylated biaryl monophosphines in up to 94% yield. Mechanistic studies confirm irreversible C–H cleavage as the rate-determining step. This work provides a sustainable and cost-effective alternative to precious-metal-based methods for the late-stage diversification of biaryl phosphine ligands.

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Publication Details

Journal
Organic Letters
Published
2026-09-11
DOI
https://doi.org/10.1021/acs.orglett.6c03293
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

PIII-Chelation-Enabled Ni(0)-Catalyzed Alkenylation of Nonacidic C–H in Biarylphosphines with Alkynes

Xiangkai Kong, Jianta Wang, Bo Li, Rong-Hua Wang et al.
Organic Letters
Catalytic C–H Functionalization Methods
article

PIII-Chelation-Enabled Ni(0)-Catalyzed Alkenylation of Nonacidic C–H in Biarylphosphines with Alkynes

Xiangkai Kong, Jianta Wang, Bo Li, Rong-Hua Wang, Ming-Bai Gou, Chun-Min Yang, Jiayu Huang, Hong-Ji Zhao, Lei Tang
article en

Abstract

Abstract A P(III)-chelation-assisted Ni(0)-catalyzed C–H alkenylation of biarylphosphines with alkynes is reported, enabling the functionalization of nonacidic arene C–H bonds without a stoichiometric base. The protocol accommodates a broad range of biarylphosphines and alkynes, affording diversely alkenylated biaryl monophosphines in up to 94% yield. Mechanistic studies confirm irreversible C–H cleavage as the rate-determining step. This work provides a sustainable and cost-effective alternative to precious-metal-based methods for the late-stage diversification of biaryl phosphine ligands.

Organic Letters
Guiyang Medical University (CN), Affiliated Hospital of Guizhou Medical University (CN)
National Natural Science Foundation of China, Guizhou Science and Technology Department, Natural Science Foundation of Guizhou Province, Guizhou Medical University
Responsible consumption and production
Openalex Percentile: Top 21%
Catalytic C–H Functionalization Methods
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