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

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.

Citation

Krzysztof R Dworakowski, Sabina Pisarek, Sidra Hassan, Dorota Gryko. Vinyl Azides as Radical Acceptors in the Vitamin B12-Catalyzed Synthesis of Unsymmetrical Ketones. Organic letters. 2021 Dec 03;23(23):9068-9072

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PMID: 34784475

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