Lewis Acid-Mediated Friedel-Crafts-Type Formylation of Alkenes with Dichloromethyl Methyl Ether in the Presence of Pyridines

Shinya Tanaka; Yuji Yoshii; Tetsutaro Hattori

doi:10.1021/acs.joc.3c02059

Lewis Acid-Mediated Friedel-Crafts-Type Formylation of Alkenes with Dichloromethyl Methyl Ether in the Presence of Pyridines

J Org Chem. 2024 Mar 1;89(5):3546-3551. doi: 10.1021/acs.joc.3c02059. Epub 2024 Feb 13.

Authors

Shinya Tanaka^{1

2}, 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 Research Institute, Tohoku University, 6-6-04 Aramaki-Aoba, Aoba-ku, Sendai 980-8579, Japan.

PMID: 38348870
DOI: 10.1021/acs.joc.3c02059

Abstract

Various alkenes are formylated with dichloromethyl methyl ether (MOMCl₂) by the combined use of SnCl₄/2,6-dibromopyridine (B1) or AgOTf/pyridine (B4) via Friedel-Crafts-type reaction. The former reagent combination is mainly applied to α,α-diarylalkenes, while the latter one is applied not only to arylalkenes but also to some alkylalkenes. Vinyl aldehydes are exclusively obtained from alkenes that can possibly afford both allyl and vinyl aldehydes.