Asymmetric C–H Dehydrogenative Alkenylation via a Photo-induced Chiral α‑Imino Radical Intermediate

Zongbin Jia, Liang Cheng, Long Zhang and Sanzhong Luo ()
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Zongbin Jia: Tsinghua University
Liang Cheng: Tsinghua University
Long Zhang: Tsinghua University
Sanzhong Luo: Tsinghua University

Nature Communications, 2024, vol. 15, issue 1, 1-8

Abstract: Abstract The direct alkenylation with simple alkenes stands out as the most ideal yet challenging strategy for obtaining high-valued desaturated alkanes. Here we present a direct asymmetric dehydrogenative α-C(sp3)-H alkenylation of carbonyls based on synergistic photoredox-cobalt-chiral primary amine catalysis under visible light. The ternary catalytic system enables the direct coupling of β-keto-carbonyls and alkenes through a cooperative radical addition-dehydrogenation process involving a chiral α-imino radical and Co(II)-metalloradical intermediate. A catalytic H-transfer process involving nitrobenzene is engaged to quench in situ generated cobalt hydride species, ensuring a chemoselective alkenylation in good yields and high enantioselectivities.

Date: 2024
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DOI: 10.1038/s41467-024-48350-w

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