A Safer Reduction of Carboxylic Acids with Titanium Catalysis

Org Lett. 2022 Nov 25;24(46):8481-8486. doi: 10.1021/acs.orglett.2c03326. Epub 2022 Nov 15.

Abstract

Ammonia-borane, shown previously to react with carboxylic acids under reflux to form primary amides, reduces acids to alcohols at room temperature in the presence of catalytic TiCl4. The process, which is tolerant of a variety of potentially reactive functional groups, including N-protected amino acids, can be employed for the selective reduction of acids in the presence of amides, nitriles and, to some extent, esters. Aliphatic acids can be selectively reduced in the presence of aromatic acids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry
  • Carboxylic Acids* / chemistry
  • Catalysis
  • Esters / chemistry
  • Titanium*

Substances

  • Amides
  • Carboxylic Acids
  • Esters
  • Titanium
  • titanium tetrachloride
  • ammonia-borane