Deoxygenative Chlorination of Aldehydes and Alcohols with Dichloromethyl Methyl Ether and TiCl4

Polat E., ÇAKICI M.

European Journal of Organic Chemistry, vol.2022, no.45, 2022 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 2022 Issue: 45
  • Publication Date: 2022
  • Doi Number: 10.1002/ejoc.202201106
  • Journal Name: European Journal of Organic Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Applied Science & Technology Source, CAB Abstracts, Chemical Abstracts Core, Chimica, MEDLINE, Index Chemicus (IC), Current Chemical Reactions (CCR)
  • Keywords: Benzal chlorides, Deoxy-chlorination, Double formylation, Geminal dichlorides, Rieche formylation, UBER ALPHA-HALOGENATHER, MEDICINAL CHEMISTRY, BENZAL HALIDES, FORMYLATION, EFFICIENT, DICHLORIDES, OLEFINATION, CONVERSION, SCOPE
  • Ataturk University Affiliated: Yes

Abstract

© 2022 Wiley-VCH GmbH.Here, we report highly efficient deoxygenative chlorination of aldehydes and alcohols with a dichloromethyl methyl ether and TiCl4 system. The method converts various aldehydes and alcohols into the desired geminal dichlorides or chlorides with good to excellent yields (up to 99 %). Combined with a subsequent Rieche formylation step using the same reagent system, this method provides an efficient approach for synthesis of aromatic dialdehydes. This strategy involves deoxy-chlorination of the aryl aldehydes followed by a second formylation of more activated benzal chloride derivatives. Dialdehydes can be easily obtained by hydrolyzing the corresponding of dichloromethyl derivative.