Oxidation of α-trifluoromethyl alcohols using a recyclable oxoammonium salt

Christopher B Kelly; Michael A Mercadante; Trevor A Hamlin; Madison H Fletcher; Nicholas E Leadbeater

doi:10.1021/jo301477s

Oxidation of α-trifluoromethyl alcohols using a recyclable oxoammonium salt

J Org Chem. 2012 Sep 21;77(18):8131-41. doi: 10.1021/jo301477s. Epub 2012 Sep 11.

Authors

Christopher B Kelly¹, Michael A Mercadante, Trevor A Hamlin, Madison H Fletcher, Nicholas E Leadbeater

Affiliation

¹ Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, Connecticut 06269-3060, USA.

PMID: 22931546
DOI: 10.1021/jo301477s

Abstract

A simple, mild method for the oxidation of α-trifluoromethyl alcohols to trifluoromethyl ketones (TFMKs) using the oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1) is described. Under basic conditions, oxidation proceeds rapidly and affords good to excellent yields of TFMKs, without concomitant formation of the hydrate. The byproduct of the oxidation, 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinyloxy (1c), is easily recovered and can be conveniently reoxidized to regenerate the oxoammonium salt.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Alcohols / chemistry*
Borates / chemistry*
Cyclic N-Oxides / chemistry*
Methanol / analogs & derivatives*
Methanol / chemistry
Molecular Structure
Oxidation-Reduction
Piperidines / chemistry*
Quaternary Ammonium Compounds / chemistry*
Salts / chemistry*

Substances

4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate
Alcohols
Borates
Cyclic N-Oxides
Piperidines
Quaternary Ammonium Compounds
Salts
trifluoromethanol
Methanol