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Photoinduced 1,2-Hydro(cyanomethylation) of Alkenes with a Cyanomethylphosphonium Ylide

Tomoya Miura*, Daisuke Moriyama, Yuuta Funakoshi, Masahiro Murakami*

*Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan, Email:,

T. Miura, D. Moriyama, Y. Funakoshi, M. Murakami, Synlett, 2019, 30, 511-514.

DOI: 10.1055/s-0037-1612230 (free Supporting Information)

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A cyanomethyl radical species generated from a cyanomethylphosphonium ylide by irradiation with visible light in the presence of an iridium complex, a thiol, and ascorbic acid enables an efficient 1,2-hydro(cyanomethylation) of alkenes. The cyanomethyl radical species adds across the C=C double bond to form an elongated alkyl radical species that accepts a hydrogen atom from the thiol.

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Key Words

alkenes, nitriles, photocatalysis, photochemistry, radicals, phosphonium ylides, hydro(cyanomethylation), ascorbic acid

ID: J72-Y2019