Mild olefin formation via bio-inspired vitamin B12 photocatalysis
| dc.citation.firstpage | 1736 | |
| dc.citation.issueNumber | 5 | |
| dc.citation.journalTitle | Chemical Science | |
| dc.citation.lastpage | 1744 | |
| dc.citation.volumeNumber | 12 | |
| dc.contributor.author | Bam, Radha | |
| dc.contributor.author | Pollatos, Alexandros S. | |
| dc.contributor.author | Moser, Austin J. | |
| dc.contributor.author | West, Julian G. | |
| dc.date.accessioned | 2021-03-09T15:44:34Z | |
| dc.date.available | 2021-03-09T15:44:34Z | |
| dc.date.issued | 2021 | |
| dc.description.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. | |
| dc.identifier.citation | Bam, 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. | |
| dc.identifier.digital | d0sc05925k | |
| dc.identifier.doi | https://doi.org/10.1039/D0SC05925K | |
| dc.identifier.uri | https://hdl.handle.net/1911/110158 | |
| dc.language.iso | eng | |
| dc.publisher | Royal Society of Chemistry | |
| dc.rights | This Open Access Article is licensed under a Creative Commons Attribution 3.0 Unported Licence | |
| dc.rights.uri | https://creativecommons.org/licenses/by/3.0/ | |
| dc.title | Mild olefin formation via bio-inspired vitamin B12 photocatalysis | |
| dc.type | Journal article | |
| dc.type.dcmi | Text | |
| dc.type.publication | publisher version |
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