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 Affiliations
Financial support for this work was provided by the Foundation for Polish Sciences (FNP TEAM POIR.04.04.00-00-4232/17-00).


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.

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

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany