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Issue 5, 2021
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Mild olefin formation via bio-inspired vitamin B12 photocatalysis

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Abstract

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

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Supplementary files

Article information


Submitted
27 Oct 2020
Accepted
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

Chem. Sci., 2021,12, 1736-1744
Article type
Edge Article

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

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