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An α‐Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung
Author(s) -
Bauer Adriano,
Di Mauro Giovanni,
Li Jing,
Maulide Nuno
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202007439
Subject(s) - umpolung , cyclopropanation , nucleophile , chemistry , reactivity (psychology) , ketone , carbocation , cationic polymerization , reagent , organic chemistry , medicinal chemistry , catalysis , medicine , alternative medicine , pathology
Abstract The reactivity of iodine(III) reagents towards nucleophiles is often associated with umpolung and cationic mechanisms. Herein, we report a general process converting a range of ketone derivatives into α‐cyclopropanated ketones by oxidative umpolung. Mechanistic investigation and careful characterization of side products revealed that the reaction follows an unexpected pathway and suggests the intermediacy of non‐classical carbocations.