Mild and chemoselective synthesis and deprotection of geminal diacetates catalyzed by titanium(IV) halides

Misuk Jung, Jieun Yoon, Hak Sung Kim, Jae Sang Ryu

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

A novel, mild, and chemoselective method was developed for the preparation of gem-diacetates from aldehydes and acetic anhydride in the presence of titanium(IV) fluoride (1-5 mol%) under solvent-free conditions at room temperature. The reaction showed a high chemoselectivity toward aldehydes in the presence of ketones. Moreover, titanium(IV) fluoride also catalyzed the deprotection of gem-diacetates to the corresponding aldehydes in water. This efficient and simple method has several benefits, including the use of an inexpensive catalyst, solvent-free conditions, mild reaction temperatures, and high yields, which make it both cost-effective and environmentally friendly.

Original languageEnglish
Article numberF04310SS
Pages (from-to)2713-2720
Number of pages8
JournalSynthesis (Germany)
Issue number16
DOIs
StatePublished - 2010

Keywords

  • acylation
  • aldehydes
  • chemoselectivity
  • deprotection
  • protecting groups

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