Cyclopropanation of Terminal Alkenes through Sequential Atom‐Transfer Radical Addition/1,3‐Elimination

Tappin, Nicholas D. C.; Michalska, Weronika; Rohrbach, Simon; Renaud, Philippe (2019). Cyclopropanation of Terminal Alkenes through Sequential Atom‐Transfer Radical Addition/1,3‐Elimination. Angewandte Chemie, 131(40), pp. 14378-14382. Wiley 10.1002/ange.201907962

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An operationally simple method to affect an atom‐transfer radical addition of commercially available ICH2Bpin 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.

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