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Lewis Base‐Promoted Ring‐Opening 1,3‐Dioxygenation of Unactivated Cyclopropanes Using a Hypervalent Iodine Reagent
Author(s) -
Gieuw Matthew H.,
Ke Zhihai,
Yeung YingYeung
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201713422
Subject(s) - hypervalent molecule , chemistry , regioselectivity , electrophile , lewis acids and bases , reagent , ring (chemistry) , iodine , benzene , diol , combinatorial chemistry , medicinal chemistry , base (topology) , organic chemistry , catalysis , mathematical analysis , mathematics
A facile and effective system has been developed for the regio‐ and chemoselective ring‐opening/electrophilic functionalization of cyclopropanes through C−C bond activation by [bis(trifluoroacetoxy)iodo]benzene with the aid of the Lewis basic promoter p ‐toluenesulfonamide. The p ‐toluenesulfonamide‐promoted system works well for a wide range of cyclopropanes, resulting in the formation of 1,3‐diol products in good yields and regioselectivity.