Issue 5, 2021

Mild olefin formation via bio-inspired vitamin B12 photocatalysis


Dehydrohalogenation, or elimination of hydrogen-halide equivalents, remains one of the simplest methods for the installation of the biologically-important olefin functionality. However, this transformation often requires harsh, strongly-basic conditions, rare noble metals, or both, limiting its applicability in the synthesis of complex molecules. Nature has pursued a complementary approach in the novel vitamin B12-dependent photoreceptor CarH, where photolysis of a cobalt–carbon bond leads to selective olefin formation under mild, physiologically-relevant conditions. Herein we report a light-driven B12-based catalytic system that leverages this reactivity to convert alkyl electrophiles to olefins under incredibly mild conditions using only earth abundant elements. Further, this process exhibits a high level of regioselectivity, producing terminal olefins in moderate to excellent yield and exceptional selectivity. Finally, we are able to access a hitherto-unknown transformation, remote elimination, using two cobalt catalysts in tandem to produce subterminal olefins with excellent regioselectivity. Together, we show vitamin B12 to be a powerful platform for developing mild olefin-forming reactions.

Graphical abstract: Mild olefin formation via bio-inspired vitamin B12 photocatalysis

Supplementary files

Article information

Article type
Edge Article
27 Oct 2020
26 Nov 2020
First published
08 Dec 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2021,12, 1736-1744

Mild olefin formation via bio-inspired vitamin B12 photocatalysis

R. Bam, A. S. Pollatos, A. J. Moser and J. G. West, Chem. Sci., 2021, 12, 1736 DOI: 10.1039/D0SC05925K

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity