Journal
SYNLETT
Volume 30, Issue 4, Pages 511-514Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1612230
Keywords
alkenes; nitriles; photocatalysis; radicals; phosphonium ylides; hydro(cyanomethylation)
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Funding
- JSPS KAKENHI [15H05756, 16K05694]
- Grants-in-Aid for Scientific Research [16K05694] Funding Source: KAKEN
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An efficient method has been developed for the 1,2-hydro(cyanomethylation) of alkenes, in which a cyanomethyl radical species is generated from a cyanomethylphosphonium ylide by irradiation with visible light in the presence of an iridium complex, a thiol, and ascorbic acid. The cyanomethyl radical species then adds across the C=C double bond of an alkene to form an elongated alkyl radical species that accepts a hydrogen atom from the thiol to produce an elongated aliphatic nitrile. The ascorbic acid acts as the reductant to complete the catalytic cycle.
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