Amine-Borane-Mediated, Nickel/Photoredox-Catalyzed Cross-Electrophile Coupling between Alkyl and Aryl Bromides

Nickel/photoredox catalysis has emerged as a powerful platform for exploring nontraditional and challenging cross-couplings. Herein, a metallaphotoredox catalytic protocol has been developed on the basis of a tertiary amine-ligated boryl radical-induced halogen atom transfer process under blue-light irradiation. A wide variety of aryl and heteroaryl bromides featuring different functional groups and pharmaceutical moieties were facilely coupled to rapidly install C(sp<sup>3</sup>)-enriched aromatic scaffolds. The compatibility of Lewis base-ligated borane with nickel catalysis was well exemplified to extend the chemical space for Ni-catalyzed cross-electrophile coupling.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-08-19
DOI
https://doi.org/10.1021/acs.joc.4c01605
Citations
15
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
3.75

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article

Amine-Borane-Mediated, Nickel/Photoredox-Catalyzed Cross-Electrophile Coupling between Alkyl and Aryl Bromides

Xian‐Chen He, Hao‐Yue Xiang, Hua Yang, Kai Chen et al.
15 citations
The Journal of Organic Chemistry
Radical Photochemical Reactions
3.75
article

Amine-Borane-Mediated, Nickel/Photoredox-Catalyzed Cross-Electrophile Coupling between Alkyl and Aryl Bromides

Xian‐Chen He, Hao‐Yue Xiang, Hua Yang, Kai Chen, Hong‐Bin Chen, Yanling Liu, Ke-Rong Li, Jie Gao
article en
15 citations

Abstract

Nickel/photoredox catalysis has emerged as a powerful platform for exploring nontraditional and challenging cross-couplings. Herein, a metallaphotoredox catalytic protocol has been developed on the basis of a tertiary amine-ligated boryl radical-induced halogen atom transfer process under blue-light irradiation. A wide variety of aryl and heteroaryl bromides featuring different functional groups and pharmaceutical moieties were facilely coupled to rapidly install C(sp<sup>3</sup>)-enriched aromatic scaffolds. The compatibility of Lewis base-ligated borane with nickel catalysis was well exemplified to extend the chemical space for Ni-catalyzed cross-electrophile coupling.

The Journal of Organic ChemistryVol. 89(17)
Central South University (CN), Shanghai Zhangjiang Laboratory (CN)
National Natural Science Foundation of China, Natural Science Foundation of Hunan Province, Fundamental Research Funds for Central Universities of the Central South University
Openalex Percentile: Top 6%
Radical Photochemical Reactions
3.75
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