Nickel/Photoredox-Catalyzed Asymmetric Three-Component Cross-Coupling To Access Enantioenriched 1,1-Diaryl(heteroaryl)alkanes
An enantioselective 1,2-dicarbofunctionalization of vinyl (hetero)arenes with alkyl bromides and aryl bromides through nickel/photoredox catalysis is described. This three-component enantioselective domino alkyl arylation of vinyl (hetero)arenes could generate a diverse array of enantioenriched 1,1-diaryl(heteroaryl)alkanes with good to excellent yields (up to 88%) and high enantioselectivities (up to 99% <i>ee</i>). This transformation could proceed well under mild conditions with excellent chemo- and regioselectivity due to the avoidance of the use of air- and moisture-sensitive organometallic reagents and stoichiometric metal reductants. Mechanistic studies suggested that the alkyl radical is generated via Ni<sup>I</sup> species or photocatalyst.
Authors
- Tingzhi Lin
- Yan‐En Wang (ORCID: https://orcid.org/0000-0001-7039-0495)
- Jianyou Mao (ORCID: https://orcid.org/0000-0003-0581-3978)
- Dan Xiong (ORCID: https://orcid.org/0000-0003-0722-8668)
- Xueying Gao
- Fei Xing (ORCID: https://orcid.org/0009-0002-9925-2293)
- Yanfeng Qiu
Institutions
- Hebei Agricultural University (CN)
- Nanjing Tech University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-08
- DOI
- https://doi.org/10.1021/acs.orglett.4c03151
- Citations
- 10
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 2.50
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Jiangsu Province