Vitamin B12-Catalyzed Dicarbofunctionalization of Bromoalkenes Under Visible Light Irradiation

Sabina Smoleń; Aleksandra Wincenciuk; Olga Drapała; Dorota Gryko

doi:10.1055/s-0040-1706602

Synthesis, Table of Contents

Synthesis 2021; 53(09): 1645-1653
DOI: 10.1055/s-0040-1706602

paper

Vitamin B₁₂-Catalyzed Dicarbofunctionalization of Bromoalkenes Under Visible Light Irradiation

Sabina Smoleń‡

^aInstitute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

,

Aleksandra Wincenciuk‡

^aInstitute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

,

Olga Drapała

^aInstitute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

^bFaculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland

,

Dorota Gryko ∗

^aInstitute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

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Abstract

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Dedicated to Professor Grzegorz Mlostoń on the occasion of his 70^th birthday.

Abstract

Vitamin B₁₂ plays a crucial role in enzymatic transformations. This natural compound proved also useful as a catalyst in numerous organic reactions. Commercial availability and lower cost than precious metal complexes, make cobalamin an attractive candidate for a broader use as a benign Co-catalyst. Herein, the vitamin B₁₂-catalyzed dicarbofuntionalization of bromoalkenes with electrophilic olefins is reported leading to substituted pyrrolidines and piperidines in decent yields after only 15 minutes under light irradiation.

Key words

cobalt - vitamin B12 - radical cyclization - Giese addition

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References

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