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Synfacts 2025; 21(07): 689
DOI: 10.1055/a-2601-4227
Metals in Synthesis

Iminothiolation of Alkenes by Metal-Free Photocatalytic Energy Transfer

Contributor(s):
Mark Lautens 
,
Mrinmay Baidya
Laskar R, Thielemann RE, Knüppe J, Hölter N, Daniliuc CG, Glorius F *. University of Münster, Germany
Photocatalytic Iminothiolation of Alkenes via Monothiocarbonate Oxime Esters.

ACS Catal. 2025;
15: 6731-6738
DOI: 10.1021/acscatal.5c01142
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Keywords

photocatalysis - energy transfer - alkene difunctionalization - radical cross-coupling

Significance

This study introduces a mild, metal-free photocatalytic method to synthesize β-aminosulfides, a valuable motif in drug discovery, via radical–radical cross-coupling of alkenes. The protocol uses bench-stable reagents, visible light, and offers excellent functional group (FG) tolerance, enabling efficient access to several functionalized aminosulfides from simple feedstocks.


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Comment

This work demonstrates a visible-light-driven, metal-free method for alkene difunctionalization via energy transfer catalysis. The protocol enables efficient imine/sulfide incorporation through cross-coupling of persistent iminyl and transient thiyl radicals, supported by mechanistic studies revealing a radical-chain pathway with broad functional group tolerance.


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Publication History

Article published online:
23 June 2025

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