Synthesis of alkyl sulfones from alkenes and tosylmethylphosphonium iodide through photo-promoted cc bond formation

Tomoya Miura; Daisuke Moriyama; Sho Miyakawa; Masahiro Murakami

doi:10.1246/CL.200530

Synthesis of alkyl sulfones from alkenes and tosylmethylphosphonium iodide through photo-promoted cc bond formation

Tomoya Miura, Daisuke Moriyama, Sho Miyakawa, Masahiro Murakami

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

1 Citation (Scopus)

Abstract

A new synthetic method for alkyl sulfones through CC bond formation between alkenes and tosylmethylphosphonium iodide is reported. A tosylmethyl radical is generated from the phosphonium iodide under irradiation of visible light with the aid of fac-Ir(ppy)₃. It undergoes regioselective 1,2-addition across the carboncarbon double bond to afford an elongated alkyl radical, which abstracts a hydrogen atom from C₆F₅SH, producing an alkyl sulfone with one-carbon extension.

Original language	English
Pages (from-to)	1382-1385
Number of pages	4
Journal	Chemistry Letters
Volume	49
Issue number	11
DOIs	https://doi.org/10.1246/CL.200530
Publication status	Published - Nov 2020
Externally published	Yes

Keywords

Phosphonium salts
Radicals
Sulfones

ASJC Scopus subject areas

Chemistry(all)

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10.1246/CL.200530

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title = "Synthesis of alkyl sulfones from alkenes and tosylmethylphosphonium iodide through photo-promoted cc bond formation",

abstract = "A new synthetic method for alkyl sulfones through CC bond formation between alkenes and tosylmethylphosphonium iodide is reported. A tosylmethyl radical is generated from the phosphonium iodide under irradiation of visible light with the aid of fac-Ir(ppy)3. It undergoes regioselective 1,2-addition across the carboncarbon double bond to afford an elongated alkyl radical, which abstracts a hydrogen atom from C6F5SH, producing an alkyl sulfone with one-carbon extension.",

keywords = "Phosphonium salts, Radicals, Sulfones",

author = "Tomoya Miura and Daisuke Moriyama and Sho Miyakawa and Masahiro Murakami",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Numbers 15H05756 (M.M.) [Scientific Research (S)] and 20H04816 (T.M.) [Scientific Research on Innovative Areas (Hybrid Catalysis)]. We thank Mr. N. Oku (Kyoto University) for his kind help in carrying out additional experiments requested by the reviewers. Publisher Copyright: {\textcopyright} 2020 The Chemical Society of Japan",

year = "2020",

month = nov,

doi = "10.1246/CL.200530",

language = "English",

volume = "49",

pages = "1382--1385",

journal = "Chemistry Letters",

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publisher = "Chemical Society of Japan",

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T1 - Synthesis of alkyl sulfones from alkenes and tosylmethylphosphonium iodide through photo-promoted cc bond formation

AU - Miura, Tomoya

AU - Moriyama, Daisuke

AU - Miyakawa, Sho

AU - Murakami, Masahiro

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Numbers 15H05756 (M.M.) [Scientific Research (S)] and 20H04816 (T.M.) [Scientific Research on Innovative Areas (Hybrid Catalysis)]. We thank Mr. N. Oku (Kyoto University) for his kind help in carrying out additional experiments requested by the reviewers. Publisher Copyright: © 2020 The Chemical Society of Japan

PY - 2020/11

Y1 - 2020/11

N2 - A new synthetic method for alkyl sulfones through CC bond formation between alkenes and tosylmethylphosphonium iodide is reported. A tosylmethyl radical is generated from the phosphonium iodide under irradiation of visible light with the aid of fac-Ir(ppy)3. It undergoes regioselective 1,2-addition across the carboncarbon double bond to afford an elongated alkyl radical, which abstracts a hydrogen atom from C6F5SH, producing an alkyl sulfone with one-carbon extension.

AB - A new synthetic method for alkyl sulfones through CC bond formation between alkenes and tosylmethylphosphonium iodide is reported. A tosylmethyl radical is generated from the phosphonium iodide under irradiation of visible light with the aid of fac-Ir(ppy)3. It undergoes regioselective 1,2-addition across the carboncarbon double bond to afford an elongated alkyl radical, which abstracts a hydrogen atom from C6F5SH, producing an alkyl sulfone with one-carbon extension.

KW - Phosphonium salts

KW - Radicals

KW - Sulfones

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DO - 10.1246/CL.200530

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VL - 49

SP - 1382

EP - 1385

JO - Chemistry Letters

JF - Chemistry Letters

IS - 11

ER -

Synthesis of alkyl sulfones from alkenes and tosylmethylphosphonium iodide through photo-promoted cc bond formation

Abstract

Keywords

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