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

Tomoya Miura; Daisuke Moriyama; Yuuta Funakoshi; Masahiro Murakami

doi:10.1055/s-0037-1612230

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

Tomoya Miura, Daisuke Moriyama, Yuuta Funakoshi, Masahiro Murakami

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	511-514
Number of pages	4
Journal	Synlett
Volume	30
Issue number	4
DOIs	https://doi.org/10.1055/s-0037-1612230
Publication status	Published - 2019
Externally published	Yes

Keywords

alkenes
hydro(cyanomethylation)
nitriles
phosphonium ylides
photocatalysis
radicals

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-0037-1612230

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

abstract = "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.",

keywords = "alkenes, hydro(cyanomethylation), nitriles, phosphonium ylides, photocatalysis, radicals",

author = "Tomoya Miura and Daisuke Moriyama and Yuuta Funakoshi and Masahiro Murakami",

note = "Funding Information: This work was supported by JSPS KAKENHI [Scientific Research (S) (15H05756) and (C) (16K05694)]JSPSKAKENHI (15H05756)JSPSKAKENHI (16K05694) Publisher Copyright: {\textcopyright} Georg Thieme Verlag KG Stuttgart New York.",

year = "2019",

doi = "10.1055/s-0037-1612230",

language = "English",

volume = "30",

pages = "511--514",

journal = "Synlett",

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T1 - Photoinduced 1,2-Hydro(cyanomethylation) of Alkenes with a Cyanomethylphosphonium Ylide

AU - Miura, Tomoya

AU - Moriyama, Daisuke

AU - Funakoshi, Yuuta

AU - Murakami, Masahiro

N1 - Funding Information: This work was supported by JSPS KAKENHI [Scientific Research (S) (15H05756) and (C) (16K05694)]JSPSKAKENHI (15H05756)JSPSKAKENHI (16K05694) Publisher Copyright: © Georg Thieme Verlag KG Stuttgart New York.

PY - 2019

Y1 - 2019

N2 - 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.

AB - 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.

KW - alkenes

KW - hydro(cyanomethylation)

KW - nitriles

KW - phosphonium ylides

KW - photocatalysis

KW - radicals

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JF - Synlett

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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