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

Org Lett. 2019 Nov 1;21(21):8509-8513. doi: 10.1021/acs.orglett.9b02688. Epub 2019 Oct 18.

Authors

Shinya Tanaka^{1

2}, Tsukasa Kunisawa¹, Yuji Yoshii¹, Tetsutaro Hattori¹

Affiliations

¹ Department of Biomolecular Engineering, Graduate School of Engineering , Tohoku University , 6-6-11 Aramaki-Aoba , Aoba-ku, Sendai 980-8579 , Japan.
² Environment Conservation Center , Tohoku University , 6-6-04 Aramaki-Aoba , Aoba-ku, Sendai 980-8579 , Japan.

PMID: 31625755
DOI: 10.1021/acs.orglett.9b02688

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.