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Direct Atom-Efficient Esterification between Carboxylic Acids and Alcohols Catalyzed by Amphoteric, Water-Tolerant TiO(acac)₂

Supporting Info

Chien-Tien Chen* and Yogesh S. Munot

Department of Chemistry, National Taiwan Normal University, Taipei, Taiwan 11650 chefv043@ntnu.edu.tw

J. Org. Chem., 2005, 70 (21), pp 8625–8627

DOI: 10.1021/jo051337s

Publication Date (Web): September 20, 2005

Address correspondence to this author. Phone: +886 2-2930-9095. Fax: +886 2-2932-4249.

Abstract

A diverse array of oxometallic species were examined as catalysts for a test direct condensation of benzoic acid and 2-phenylethanol in 1:1 stoichiometry. Besides group IVB MOCl₂−xH₂O and TiOX₂−xH₂O, group VB VOCl₂−xTHF and group IVB TiO(acac)₂ were found to be the most efficient and water-tolerant catalysts for the test reaction. The new neutral catalytic protocol with the optimal TiO(acac)₂ tolerates many stereo/electronic structural variations in both (di)acid (1°−3° alkyl and aryl) and (di)alcohol (1°, 2° alkyl, and aryl) components with high chemoselectivity.