Nucleophilic ortho allylation of aryl and heteroaryl sulfoxides |
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Authors: | Eberhart Andrew J Imbriglio Jason E Procter David J |
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Institution: | School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK. |
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Abstract: | Aryl and heteroaryl sulfoxides undergo ortho allylation upon treatment with Tf(2)O and allylsilanes. The method complements the use of sulfoxides to direct ortho-metalation and reaction with electrophiles as it allows allylic carbon nucleophiles to be added ortho to the directing group in a metal-free process. The versatile sulfide adducts can be selectively manipulated using various methods including Kumada-Corriu cross-coupling of the organosulfanyl group. |
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