5 years ago

Synthesis of Benzoxazoles Using Electrochemically Generated Hypervalent Iodine

Synthesis of Benzoxazoles Using Electrochemically Generated Hypervalent Iodine
Edgars Suna, Robert Francke, Jan Noetzel, Olesja Koleda, Michael Roemelt, Timo Broese
The indirect (“ex-cell”) electrochemical synthesis of benzoxazoles from imines using a redox mediator based on the iodine(I)/iodine(III) redox couple is reported. Tethering the redox-active iodophenyl subunit to a tetra-alkylammonium moiety allowed for anodic oxidation to be performed without supporting electrolyte. The mediator salt can be easily recovered and reused. Our “ex-cell” approach toward the electrosynthesis of benzoxazoles is compatible with a range of redox-sensitive functional groups. An unprecedented concerted reductive elimination mechanism for benzoxazole formation is proposed on the basis of control experiments and DFT calculations.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01686

DOI: 10.1021/acs.joc.7b01686

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