Journal
TETRAHEDRON
Volume 68, Issue 44, Pages 9068-9075Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.08.051
Keywords
Selective O-benzoylation; Inverse selectivity; Phenolic alcohols; Aminobenzyl alcohols; PMDETA-catalyzed; Organocatalyst; Trichloromethyl phenyl ketone
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Funding
- University Grant Commission, New Delhi
- Council of Scientific Research, New Delhi
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Trichloromethyl phenyl ketone benzoylates primary and secondary aliphatic alcoholic groups in compounds also containing a phenolic group in the presence of 2-10 mol % of PMDETA organocatalyst at room temperature in high yields and excellent selectivity. It also shows the potential to selectively benzoylate primary alcoholic groups of aminoarylalkanols and primary-secondary diols as well as primary amino group of alkyl amines in the presence of aryl amines under similar conditions. A rationale for the selectivity and efficiency of the reaction has been provided. (C) 2012 Elsevier Ltd. All rights reserved.
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