Acylation of Alkenes with the Aid of AlCl3 and 2,6-Dibromopyridine

Shinya Tanaka; Tsukasa Kunisawa; Yuji Yoshii; Tetsutaro Hattori

doi:10.1021/acs.orglett.9b02688

Acylation of Alkenes with the Aid of AlCl₃ and 2,6-Dibromopyridine

Shinya Tanaka, Tsukasa Kunisawa, Yuji Yoshii, Tetsutaro Hattori

ENG - Biomolecular Engineering

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

6 Citations (Scopus)

Abstract

Friedel-Crafts-type acylation of alkenes with acyl chlorides has been successfully conducted with a wide substrate scope by the combined use of AlCl₃ and 2,6-dibromopyridine. Trisubstituted alkenes afford allylketones or vinylketones depending on the presence or absence of hydrogen atom(s) at the β-position to the acylation site, while monosubstituted alkenes exclusively afford vinylketones.

Original language	English
Pages (from-to)	8509-8513
Number of pages	5
Journal	Organic letters
Volume	21
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.9b02688
Publication status	Published - 2019 Nov 1

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.9b02688

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title = "Acylation of Alkenes with the Aid of AlCl3 and 2,6-Dibromopyridine",

abstract = "Friedel-Crafts-type acylation of alkenes with acyl chlorides has been successfully conducted with a wide substrate scope by the combined use of AlCl3 and 2,6-dibromopyridine. Trisubstituted alkenes afford allylketones or vinylketones depending on the presence or absence of hydrogen atom(s) at the β-position to the acylation site, while monosubstituted alkenes exclusively afford vinylketones.",

author = "Shinya Tanaka and Tsukasa Kunisawa and Yuji Yoshii and Tetsutaro Hattori",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Number K17K14443. Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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T1 - Acylation of Alkenes with the Aid of AlCl3 and 2,6-Dibromopyridine

AU - Tanaka, Shinya

AU - Kunisawa, Tsukasa

AU - Yoshii, Yuji

AU - Hattori, Tetsutaro

PY - 2019/11/1

Y1 - 2019/11/1

N2 - Friedel-Crafts-type acylation of alkenes with acyl chlorides has been successfully conducted with a wide substrate scope by the combined use of AlCl3 and 2,6-dibromopyridine. Trisubstituted alkenes afford allylketones or vinylketones depending on the presence or absence of hydrogen atom(s) at the β-position to the acylation site, while monosubstituted alkenes exclusively afford vinylketones.

AB - Friedel-Crafts-type acylation of alkenes with acyl chlorides has been successfully conducted with a wide substrate scope by the combined use of AlCl3 and 2,6-dibromopyridine. Trisubstituted alkenes afford allylketones or vinylketones depending on the presence or absence of hydrogen atom(s) at the β-position to the acylation site, while monosubstituted alkenes exclusively afford vinylketones.

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ER -

Acylation of Alkenes with the Aid of AlCl₃ and 2,6-Dibromopyridine

Abstract

ASJC Scopus subject areas

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