Nickel-Catalyzed Photoredox Allenylation of Alkyl Halides
We report a dual Ni/photoredox-catalyzed cross-coupling method for propargyl carbonates and nonactivated alkyl bromides, facilitating the synthesis of a variety of substituted allenes under mild and practical conditions. Mechanistically, the reaction integrates Ni-catalyzed activation of the propargyl electrophile via S<sub>N</sub><sup>2</sup>' oxidative addition at Ni(I) with silyl radical-induced activation of the alkyl halide through halogen-atom transfer. This methodology provides a gentle approach for introducing allenyl groups into complex halogenated aliphatic molecules, offering further opportunities for derivatization.
Authors
- Tingjun Hu
- Abderrahmane Amgoune (ORCID: https://orcid.org/0000-0002-6195-1411)
- Didier Bouyssi
- Vincent Fagué
- Nuno Monteiro (ORCID: https://orcid.org/0000-0003-2248-6681)
- Camille Beluze
- Oho Eliantine Kambire
Institutions
- Université Claude Bernard Lyon 1 (FR)
- Centre National de la Recherche Scientifique (FR)
- Institut Universitaire de France (FR)
- Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (FR)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-25
- DOI
- https://doi.org/10.1021/acs.orglett.4c03512
- Citations
- 6
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 1.50
Funders
- China Scholarship Council
- Centre National de la Recherche Scientifique
- Institut Universitaire de France
- Université Claude Bernard Lyon 1