Nitrogen-to-Carbon Single Atom Point Mutation of Pyridine N-Oxides

24 January 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Single-atom editing has emerged as a powerful process for altering molecular structures with precision. Within this growing class of transformations, reactions that replace one atom for another in heterocycles, while desirable, remain limited. We report the development of a transformation that achieves an N-to-C atom swap in pyridine N-oxides utilizing a sulfoxide-derived anion as a carbon source. This ‘point mutation’ exhibits good functional group tolerance and replaces the N-oxide moiety with either unsubstituted, substituted, or isotopically labeled carbon atoms in a single laboratory operation.


skeletal editing


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