Synthesis 2017; 49(13): 2928-2932
DOI: 10.1055/s-0036-1588439
special topic
© Georg Thieme Verlag Stuttgart · New York

Iodine(III)-Mediated Oxidative Hydrolysis of Haloalkenes: Investigation of the Effect of Iodine(III) Reagents

Robin Dagenais
Université de Sherbrooke, Department of Chemistry, 2500 boul. de l’Université, Sherbrooke (Québec), J1K 2R1, Canada   Fax: Fax +1(819)8218017   Email: claude.legault@usherbrooke.ca
,
Antoine Jobin-Des Lauriers
Université de Sherbrooke, Department of Chemistry, 2500 boul. de l’Université, Sherbrooke (Québec), J1K 2R1, Canada   Fax: Fax +1(819)8218017   Email: claude.legault@usherbrooke.ca
,
Université de Sherbrooke, Department of Chemistry, 2500 boul. de l’Université, Sherbrooke (Québec), J1K 2R1, Canada   Fax: Fax +1(819)8218017   Email: claude.legault@usherbrooke.ca
› Author Affiliations
Further Information

Publication History

Received: 31 March 2017

Accepted after revision: 04 May 2017

Publication Date:
07 June 2017 (online)

Published as part of the Special Topic Modern Strategies with Iodine in Synthesis

Abstract

The iodine(III)-mediated oxidative transposition of vinyl halides to the corresponding α-halo ketones has been recently reported. The method is high yielding and offers good substrate scope. The investigation of other iodine(III) reagents to promote this reaction is described. The newly developed protocol reduces the number of waste products formed in the synthetic transformation. A structure–reactivity relationship study of numerous [hydroxy(tosyloxy)iodo]arenes toward haloalkenes is reported. The results highlight the challenge of obtaining a chemoselective reaction using these reagents.

 
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