Issue 11, 2024

Nickel metallaphotoredox-catalyzed C–O bond activation/Csp2–Csp3 coupling enabled by phosphine

Abstract

The free alcohol C–O bond activation strategy to generate alkyl radicals, which would serve as a large pool of coupling partners in transition-metal catalysis, remains limited, challenging, and in high demand. Herein, a novel and general nickel/photoredox dual catalysis platform for benzyl alcohol C–O bond activation/Csp2–Csp3 cross coupling of heteroaromatic benzothiazolyl bromide and free benzyl alcohol, enabled by the catalytic generation of an alkyl radical, is reported. The manifold features of this protocol include operational simplicity, high-functional-group tolerance, and broad substrate scope. Notably, late-stage diversification of architecturally intriguing drugs or bioactive molecules further showcases the synthetical potential of this protocol.

Graphical abstract: Nickel metallaphotoredox-catalyzed C–O bond activation/Csp2–Csp3 coupling enabled by phosphine

Supplementary files

Article information

Article type
Research Article
Submitted
15 Feb 2024
Accepted
30 Mar 2024
First published
02 Apr 2024

Org. Chem. Front., 2024,11, 3058-3065

Nickel metallaphotoredox-catalyzed C–O bond activation/Csp2–Csp3 coupling enabled by phosphine

J. Fang, Z. Jian, H. Liu, Y. Wang, X. Yu, Z. Mou and H. Wang, Org. Chem. Front., 2024, 11, 3058 DOI: 10.1039/D4QO00310A

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