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

Polat, Emrah; Çakıcı, Murat

doi:10.1002/ejoc.202201106

Makale Tam Makale Uluslararası 2022

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

Emrah Polat, Murat Çakıcı

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY Sayı 45 · 01.12.2022

DOI ile aç

Özet

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.

Anahtar kelimeler

CONVERSION MEDICINAL CHEMISTRY EFFICIENT FORMYLATION Benzal chlorides Deoxy-chlorination Double formylation Geminal dichlorides Rieche formylation UBER ALPHA-HALOGENATHER BENZAL HALIDES DICHLORIDES OLEFINATION SCOPE

Atıf için künye

Polat, E., & Çakıcı, M. (2022). Deoxygenative Chlorination of Aldehydes and Alcohols with Dichloromethyl Methyl Ether and TiCl4. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(45). https://doi.org/10.1002/ejoc.202201106

BibTeX

@article{polat2022-72647,
  author = {Polat, Emrah and Çakıcı, Murat},
  title = {Deoxygenative Chlorination of Aldehydes and Alcohols with Dichloromethyl Methyl Ether and TiCl4},
  journal = {EUROPEAN JOURNAL OF ORGANIC CHEMISTRY},
  year = {2022},
  number = {45},
  issn = {1434-193X},
  doi = {10.1002/ejoc.202201106},
  url = {https://akademik.atauni.edu.tr/yayinlar/72647-deoxygenative-chlorination-of-aldehydes-and-alcohols-with-dichloromethyl-methyl}
}