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Vinyl Azides as Radical Acceptors in the Vitamin B₁₂-Catalyzed Synthesis of Unsymmetrical Ketones.

ABSTRACT: Vinyl azides are very reactive species and as such are useful building blocks, in particular, in the synthesis of N-heterocycles. They can also serve as precursors of ketones. These form in reactions of vinyl azides with nucleophiles or radicals. We have found, however, that under light irradiation vitamin B₁₂ catalyzes the reaction of vinyl azides with electrophiles to afford unsymmetrical carbonyl compounds in decent yields. Mechanistic studies revealed that alkyl radicals are key intermediates in this transformation.

SUBMITTER: Dworakowski KR

PROVIDER: S-EPMC8650103 | biostudies-literature |

REPOSITORIES: biostudies-literature

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