Mild olefin formation via bio-inspired vitamin B12 photocatalysis

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dc.citation.firstpage1736en_US
dc.citation.issueNumber5en_US
dc.citation.journalTitleChemical Scienceen_US
dc.citation.lastpage1744en_US
dc.citation.volumeNumber12en_US
dc.contributor.authorBam, Radhaen_US
dc.contributor.authorPollatos, Alexandros S.en_US
dc.contributor.authorMoser, Austin J.en_US
dc.contributor.authorWest, Julian G.en_US
dc.date.accessioned2021-03-09T15:44:34Zen_US
dc.date.available2021-03-09T15:44:34Zen_US
dc.date.issued2021en_US
dc.description.abstractDehydrohalogenation, 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.en_US
dc.identifier.citationBam, Radha, Pollatos, Alexandros S., Moser, Austin J., et al.. "Mild olefin formation via bio-inspired vitamin B12 photocatalysis." <i>Chemical Science,</i> 12, no. 5 (2021) Royal Society of Chemistry: 1736-1744. https://doi.org/10.1039/D0SC05925K.en_US
dc.identifier.digitald0sc05925ken_US
dc.identifier.doihttps://doi.org/10.1039/D0SC05925Ken_US
dc.identifier.urihttps://hdl.handle.net/1911/110158en_US
dc.language.isoengen_US
dc.publisherRoyal Society of Chemistryen_US
dc.rightsThis Open Access Article is licensed under a Creative Commons Attribution 3.0 Unported Licenceen_US
dc.rights.urihttps://creativecommons.org/licenses/by/3.0/en_US
dc.titleMild olefin formation via bio-inspired vitamin B12 photocatalysisen_US
dc.typeJournal articleen_US
dc.type.dcmiTexten_US
dc.type.publicationpublisher versionen_US
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