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Alkene Carboarylation through Catalyst-Free, Visible Light-Mediated Smiles Rearrangement
David M Whalley1, Hung A Duong2, Michael F Greaney1
1School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK.
Abstract:
A light-mediated Truce-Smiles arylative rearrangement is described that proceeds in the absence of any photocatalyst. The protocol creates two C-C bonds from simple starting materials, with the installation of an aryl ring and a difluoroacetate moiety across unactivated alkenes. The reaction proceeds via a radical mechanism, utilizing a light-mediated reduction of ethyl bromodifluoroacetate by N,N,N',N'-tetramethylethylenediamine (TMEDA) to set up intermolecular addition to an unactivated alkene, followed by Truce-Smiles rearrangement.
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