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Synfacts 2025; 21(07): 693
DOI: 10.1055/a-2601-5762
Metals in Synthesis

Dual Photocatalysis for Remote C(sp3)–H Acylation

Contributor(s):
Mark Lautens 
,
Mrinmay Baidya
Li D, Wei J, Ren L, Zhou L, Huang L, Yu Y, Wei S *, Hao N, Wang J, Yang L, Pan X, Fu Q *, Lu J *. Southwest Medical University, Luzhou, P. R. China
Dual Photoexcited Palladium and Photoredox-Catalyzed Remote C(sp3)–H Acylation of Hydroxyamides.

Org. Lett. 2025;
27: 4479-4484
DOI: 10.1021/acs.orglett.5c00881
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Keywords

photoredox catalysis - C–H activation - amidyl radicals - remote C(sp3)–H acylation

Significance

This work reports a dual photoexcited palladium/photoredox system for the remote C(sp3)–H acylation of amides without external acylating agents. The method features high atom economy, broad functional group (FG) tolerance, and efficient radical-mediated C–C bond formation.


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Comment

Mechanistic studies (kinetic isotope effect and crossover) support a fast 1,5-HAT (hydrogen atom transfer) and Pd(I)/alkyl-radical recombination, excluding carbanion intermediates. A gram-scale synthesis and late-stage acylation of a synthesized product highlight the utility of the method.


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Publication History

Article published online:
23 June 2025

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