Alkene Carboarylation through Catalyst-Free,Visible Light-Mediated Smiles Rearrangement |
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| Authors: | David M. Whalley Hung A. Duong Prof. Michael F. Greaney |
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| Affiliation: | 1. School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL UK;2. Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 8 Biomedical Grove, Neuros, #07-01, Singapore, 138665 Singapore |
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| 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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| Keywords: | aromatic substitution arylation photochemistry radical reactions rearrangement |
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