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Iodine(III)-Mediated Oxidative Hydrolysis of Haloalkenes: Access to α-Halo Ketones by a Release-and-Catch Mechanism

Antoine Jobin-Des Lauriers and Claude Y. Legault*

*University of Sherbrooke, Department of Chemistry, Centre in Green Chemistry and Catalysis, 2500 boul. de l’Université, Sherbrooke, Québec J1K 2R1, Canada, Email: claude.legaultusherbrooke.ca

A. Jobin-Des Lauriers, C. Y. Legault, Org. Lett., 2016, 18, 108-111.

DOI: 10.1021/acs.orglett.5b03345 (free Supporting Information)


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Abstract

HTIB mediates an oxidative transposition of vinyl halides to provide α-halo ketones as useful and polyvalent synthetic precursors. Insights into the mechanism and an enantioselective transformation are reported too.

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Study of the Reactivity of [Hydroxy(tosyloxy)iodo]benzene Toward Enol Esters to Access α-Tosyloxy Ketones

B. Basdevant, C. Y. Legault, J. Org. Chem., 2015, 80, 6897-6902.


Key Words

HTIB, α-bromination, α-chlorination, oxidative hydrolysis


ID: J54-Y2016