NHCs and Visible Light Co-catalyzed 1,4-Sulfonylacylation of 1,3-Enynes for Tetrasubstituted Allenyl Ketones

21 October 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


The modulation of selectivity of highly reactive carbon radical cross-coupling for the construction of C-C bonds represents a challenging task in organic chemistry. N-Heterocyclic carbenes (NHCs) catalyzed radical transformations opened a new avenue for acyl radical cross-coupling chemistry. With this method, highly selective cross-coupling of acyl radical with alkyl radical for efficient construction of C-C bonds were succussfully realized. However, the cross-coupling reaction of acyl radical with vinyl radicals represents an uncharted domain. We herein describe NHCs and photocatalysis co-catalyzed radical 1,4-sulfonylacylation of 1,3-enynes, providing structurally diversified valuable tetrasubstituted allenyl ketones. Mechanistic studies indicated that ketyl radicals are formed from aroyl fluorides via oxidative quenching process of excited photocatalysis, allenyl radicals are generated from chemo specific sulfonyl radical addition to the 1,3-enynes, finally, unprecedented key allenyl and ketyl radical cross-coupling provides tetrasubstituted allenyl ketones.


radical/radical cross-coupling
conjugated enynes
remote sulfonylacylation

Supplementary materials

Supporting Information
Supporting Information for "NHCs and Visible Light Co-catalyzed 1,4-Sulfonylacylation of 1,3-Enynes for Tetrasubstituted Allenyl Ketones"


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