Indirect Anodic Monofluorodesulfurization of β-Phenylsulfenyl β-lactams Using a Triarylamine Mediator

Toshio Fuchigami; Makio Tetsu; Toshiki Tajima; Hideki Ishii

doi:10.1055/s-2001-16063

Synlett 2001; 2001(8): 1269-1271
DOI: 10.1055/s-2001-16063

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Indirect Anodic Monofluorodesulfurization of β-Phenylsulfenyl β-lactams Using a Triarylamine Mediator

Toshio Fuchigami^* , Makio Tetsu, Toshiki Tajima, Hideki Ishii

^*Department of Electronic Chemistry, Tokyo Institute of Technology, Nagatsuta, Midori-ku, Yokohama 226-8502, Japan; Fax + 81 45 921 10 89; E-mail: fuchi@echem.titech.ac.jp

Abstract

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Indirect anodic oxidation of β-phenylsulfenyl β-lactams was carried out using a catalytic amount of triarylamine as a mediator in acetonitrile containing fluoride ions; regioselective monofluorodesulfurization took place to give the corresponding β-fluorinated β-lactams in good yields. This is the first successful example of triarylamine-mediated anodic fluorodesulfurization.

electrochemical fluorination - fluorodesulfurization - β-lactam - mediator - fluoride salt

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