Yi B,
Zhang H,
Pan C,
Lu J,
Li Q,
Yuan K,
Xing Q,
Chen W,
An X,
Kandegama W *,
Zhang G *,
Guo R *.
Wayamba University of Sri Lanka, Gonawila, Sri Lanka, and Central China Normal University,
Wuhan, P. R. China
Hydroalkylation of Unactivated Alkenes with Amides via Photoredox Catalysis and Triple
Hydrogen Atom Transfer.
Angew. Chem. Int. Ed. 2025;
64: e202516794
DOI:
10.1002/anie.202516794
Keywords
triple HAT - α-olefins - unactivated - amide - radicals
Significance
The authors present a novel photocatalytic approach for the hydroalkylation of unactivated
alkenes with amides. The transformation operates via a triple hydrogen-atom transfer
(HAT) pathway, enabling selective generation of relatively weak α-carbonyl radicals.
Through finetuning of radical polarity match/mismatch effects, the method facilitates
efficient C(sp3)–C(sp3) bond formation, thereby granting access to valuable products in good yields (50–75 %).
Comment
Traditional radical hydroalkylation strategies of alkenes have been largely limited
to highly activated carbonyl substrates, such as 1,3-dicarbonyls and cyanoacetates.
By contrast, the present study reports a mild, photocatalyzed hydroalkylation protocol
that enables the coupling of unactivated alkenes with amides, demonstrating a broader
substrate scope and remarkable functional group tolerance.
