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Cyclopropanation of Terminal Alkenes through Sequential Atom‐Transfer Radical Addition/1,3‐Elimination
Author(s) -
Tappin Nicholas D. C.,
Michalska Weronika,
Rohrbach Simon,
Renaud Philippe
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201907962
Subject(s) - cyclopropanation , cyclopropane , chemistry , alkene , iodide , terminal (telecommunication) , fluoride , medicinal chemistry , organic chemistry , stereochemistry , catalysis , inorganic chemistry , ring (chemistry) , telecommunications , computer science
An operationally simple method to affect an atom‐transfer radical addition of commercially available ICH 2 Bpin to terminal alkenes has been developed. The intermediate iodide can be transformed in a one‐pot process into the corresponding cyclopropane upon treatment with a fluoride source. This method is highly selective for the cyclopropanation of unactivated terminal alkenes over non‐terminal alkenes and electron‐deficient alkenes. Due to the mildness of the procedure, a wide range of functional groups such as esters, amides, alcohols, ketones, and vinylic cyclopropanes are well tolerated.