Cyano group translocation to alkenyl C(sp2)–H site by radical cation catalysis

Luyang Li, Tongyan Yu, Kemeng Du and Pan Xu ()
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Luyang Li: Southeast University
Tongyan Yu: Southeast University
Kemeng Du: Southeast University
Pan Xu: Southeast University

Nature Communications, 2025, vol. 16, issue 1, 1-9

Abstract: Abstract Achieving the direct translocation of a functional group to unactivated C–H sites within a molecule, while maintaining its structural integrity, presents a notable challenge in the realm of organic synthesis. Here, we report that photocatalytic quinuclidine-based radical cation catalysis can enable selective 1,4-cyano translocation to alkenyl C(sp2)–H sites without imparting any extraneous modifications. The approach leverages N-centered radical cations as catalysts to facilitate both radical translocation and ionic elimination, thereby restoring the double bond and enabling positional exchange between a CN group and a C(sp2)–H bond. This results in the formation of alkenyl cyanide, a versatile linchpin that can easily undergo substitution reactions with a wide range of nucleophiles then lead to diverse difunctionalizations of alkenes. Consequently, this CN translocation approach complements the existing state-of-the-art method of radical-induced alkene 1,2-difunctionalization via functional group translocation.

Date: 2025
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DOI: 10.1038/s41467-025-62585-1

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