Remote Arylative Substitution of Alkenes Possessing an Acetoxy Group via β-Acetoxy Elimination

Kazuma Muto; Takaaki Kumagai; Fumitoshi Kakiuchi; Takuya Kochi

doi:10.1002/anie.202111396

Remote Arylative Substitution of Alkenes Possessing an Acetoxy Group via β-Acetoxy Elimination

Kazuma Muto, Takaaki Kumagai, Fumitoshi Kakiuchi, Takuya Kochi

Department of Chemistry

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

6 Citations (Scopus)

Abstract

Palladium-catalyzed remote arylative substitution was achieved for the reaction of arylboronic acids with alkenes possessing a distant acetoxy group to provide arylation products having an alkene moiety at the remote position. The use of β-acetoxy elimination as a key step in the catalytic cycle allowed for regioselective formation of unstabilized alkenes after chain walking. This reaction was applicable to various arylboronic acids as well as alkene substrates.

Original language	English
Pages (from-to)	24500-24504
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	60
Issue number	46
DOIs	https://doi.org/10.1002/anie.202111396
Publication status	Published - 2021 Nov 8

Keywords

alkenes
arylation
chain walking
palladium
β-acetoxy elimination

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.202111396

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title = "Remote Arylative Substitution of Alkenes Possessing an Acetoxy Group via β-Acetoxy Elimination",

abstract = "Palladium-catalyzed remote arylative substitution was achieved for the reaction of arylboronic acids with alkenes possessing a distant acetoxy group to provide arylation products having an alkene moiety at the remote position. The use of β-acetoxy elimination as a key step in the catalytic cycle allowed for regioselective formation of unstabilized alkenes after chain walking. This reaction was applicable to various arylboronic acids as well as alkene substrates.",

keywords = "alkenes, arylation, chain walking, palladium, β-acetoxy elimination",

author = "Kazuma Muto and Takaaki Kumagai and Fumitoshi Kakiuchi and Takuya Kochi",

note = "Funding Information: This work was supported, in part, by JSPS KAKENHI Grant Numbers, JP18H01985 (Grant‐in‐Aid for Scientific Research (B)), and JP15KT0069 (Grant‐in‐Aid for Scientific Research (B)) as well as the Asahi Glass Foundation. K.M. is also grateful for support by the Keio University Doctorate Student Grant‐in‐Aid Program from Ushioda Memorial Fund. Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

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AU - Muto, Kazuma

AU - Kumagai, Takaaki

AU - Kakiuchi, Fumitoshi

AU - Kochi, Takuya

N1 - Funding Information: This work was supported, in part, by JSPS KAKENHI Grant Numbers, JP18H01985 (Grant‐in‐Aid for Scientific Research (B)), and JP15KT0069 (Grant‐in‐Aid for Scientific Research (B)) as well as the Asahi Glass Foundation. K.M. is also grateful for support by the Keio University Doctorate Student Grant‐in‐Aid Program from Ushioda Memorial Fund. Publisher Copyright: © 2021 Wiley-VCH GmbH

PY - 2021/11/8

Y1 - 2021/11/8

N2 - Palladium-catalyzed remote arylative substitution was achieved for the reaction of arylboronic acids with alkenes possessing a distant acetoxy group to provide arylation products having an alkene moiety at the remote position. The use of β-acetoxy elimination as a key step in the catalytic cycle allowed for regioselective formation of unstabilized alkenes after chain walking. This reaction was applicable to various arylboronic acids as well as alkene substrates.

AB - Palladium-catalyzed remote arylative substitution was achieved for the reaction of arylboronic acids with alkenes possessing a distant acetoxy group to provide arylation products having an alkene moiety at the remote position. The use of β-acetoxy elimination as a key step in the catalytic cycle allowed for regioselective formation of unstabilized alkenes after chain walking. This reaction was applicable to various arylboronic acids as well as alkene substrates.

KW - alkenes

KW - arylation

KW - chain walking

KW - palladium

KW - β-acetoxy elimination

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Remote Arylative Substitution of Alkenes Possessing an Acetoxy Group via β-Acetoxy Elimination

Abstract

Keywords

ASJC Scopus subject areas

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