Oxidation of Benzylic Alcohols and Benzaldehydes with the SelectfluorTM Reagent F-TEDA-BF4 {1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)}

R. Eric Banks; Nicholas J. Lawrence; Allan L. Popplewell

doi:10.1055/s-1994-23021

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Synlett 1994; 1994(10): 831-832
DOI: 10.1055/s-1994-23021

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Oxidation of Benzylic Alcohols and Benzaldehydes with the Selectfluor^TM Reagent F-TEDA-BF₄ {1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)}

R. Eric Banks^* , Nicholas J. Lawrence, Allan L. Popplewell

^*Chemistry Department, University of Manchester Institute of Science and Technology, Manchester, M60 1QD, UK.

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Publication Date:
22 March 2002 (online)

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Substituted benzylic alcohols and aromatic aldehydes can be oxidised efficiently to substituted benzaldehydes and benzoic acids respectively with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate); the latter conversion proceeds via acid fluorides, which enables aldehydes to function as acylating agents in a one-pot procedure.