Spectroscopic characterization of (diiodomethyl)zinc iodide: application to the stereoselective synthesis and functionalization of iodocyclopropanesElectronic supplementary information (ESI) available. CCDC 1554344. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7cc04348a

Herein is described an improved synthetic route to enantio- and diastereoenriched iodocyclopropylmethanols using (diiodomethyl)zinc iodide etherate as the active species. The products obtained by this methodology were successfully functionalized by Suzuki-Miyaura cross-coupling reactions. A Buchwald-type palladium precatalyst allowed access to highly substituted and stereo-enriched cyclopropanes without requiring a protecting group. Herein are described more efficient methodologies for the synthesis of highly substituted cyclopropanes as well as the first characterization of a diiodomethylzinc carbenoid.