title: α-Difluoromethylation on sp(3) Carbon of Nitriles Using Fluoroform and Ruppert-Prakash Reagent.
abstract: Difluoromethylation on sp(3) carbon of various nitrile compounds with lithium base and fluoroform (CF3H), which is an ideal difluoromethylating reagent, is shown to provide the α-difluoromethylated nitrile products with an all-carbon quaternary center in moderate to high yields. The Ruppert-Prakash reagent (CF3TMS) is also applicable to the reaction, affording the α-siladifluoromethylated nitrile products, which can be utilized for sequential carbon-carbon bond-forming reactions. These reactions using 1.1 equiv of lithium base, 1.5-2.0 equiv of CF3H or CF3TMS, and easily accessible nitrile derivatives are completed in only a few minutes, resulting in the formation of valuable difluoromethylated compounds.
authors.affiliation: Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology , O-okayama, Meguro-ku, Tokyo 152-8552, Japan.
authors.forename: Kohsuke
authors.initials: K
authors.lastname: Aikawa
authors.affiliation: Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology , O-okayama, Meguro-ku, Tokyo 152-8552, Japan.
authors.forename: Kenichi
authors.initials: K
authors.lastname: Maruyama
authors.affiliation: Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology , O-okayama, Meguro-ku, Tokyo 152-8552, Japan.
authors.forename: Kazuya
authors.initials: K
authors.lastname: Honda
authors.affiliation: Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology , O-okayama, Meguro-ku, Tokyo 152-8552, Japan.
authors.forename: Koichi
authors.initials: K
authors.lastname: Mikami