362474-71-3Relevant articles and documents
Nickel Nanoparticle Catalyzed Mono- and Di-Reductions of gem-Dibromocyclopropanes Under Mild, Aqueous Micellar Conditions
Akkachairin, Bhornrawin,Cortes-Clerget, Margery,Gallou, Fabrice,Kincaid, Joseph R. A.,Lipshutz, Bruce H.,Singhania, Vani,Wood, Alex B.
, p. 17587 - 17593 (2020)
Mild mono- and di-hydrodehalogenative reductions of gem-dibromocyclopropanes are described, providing an easy and green approach towards the synthesis of cyclopropanes. The methodology utilizes 0.5–5 mol % TMPhen-nickel as the catalyst, which, when activated with a hydride source such as sodium borohydride, cleanly and selectively dehalogenates dibromocyclopropanes. Double reduction proceeds in a single operation at temperatures between 20–45 °C and at atmospheric pressure in an aqueous designer surfactant medium. At lower loading and either in the absence of ligand or in the presence of 2,2′-bipyridine, this new technology can also be used to gain access to not only monobrominated cyclopropanes, interesting building blocks for further use in synthesis, but also mono- or di-deuterated analogues. Taken together, this base-metal-catalyzed process provides access to cyclopropyl-containing products and is achieved under environmentally responsible conditions.
