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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‡
a   Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
,
Aleksandra Wincenciuk‡
a   Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
,
Olga Drapała
a   Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
b   Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland
,
Dorota Gryko  ∗
a   Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
› Author AffiliationsFinancial support for this work was provided by the Foundation for Polish Sciences (FNP TEAM POIR.04.04.00-00-4232/17-00).
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Dedicated to Professor Grzegorz Mlostoń on the occasion of his 70th 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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706602.
  • Supporting Information


Publication History

Received: 31 August 2020

Accepted after revision: 02 November 2020

Article published online:
23 November 2020

© 2020. Thieme. All rights reserved

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