Literature DB >> 22931546

Oxidation of α-trifluoromethyl alcohols using a recyclable oxoammonium salt.

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

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.

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Year:  2012        PMID: 22931546     DOI: 10.1021/jo301477s

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  1 in total

1.  Synthesis of 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate and 4-acetamido-(2,2,6,6-tetramethyl-piperidin-1-yl)oxyl and their use in oxidative reactions.

Authors:  Michael A Mercadante; Christopher B Kelly; James M Bobbitt; Leon J Tilley; Nicholas E Leadbeater
Journal:  Nat Protoc       Date:  2013-03-07       Impact factor: 13.491

  1 in total

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