Synthesis of the benzhydryl motif via a Suzuki-Miyaura coupling of arylboronic acids and 3-chloroacrylonitriles.
[reaction: see text] A simple two-step procedure for synthesizing functionalized benzhydrylamines is described. The first step involves a Suzuki-Miyaura coupling reaction between arylboronic acids and 3-chloro-3-arylacrylonitriles at 45 degrees C. A variety of boronic acids and substituted acrylonitriles can be used for the reaction. The resulting 3,3-diaryl-substituted acrylonitriles can be converted into their corresponding Boc-protected amines by catalytic hydrogenation.
Taylor
Steven J
SJ
Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, USA. staylor@rdg.boehringer-ingelheim.com
Netherton
Matthew R
MR
D000181:Acrylonitrile / Q000737:chemistry*; D001554:Benzene / Q000138:chemical synthesis / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D015394:Molecular Structure
D001897:Boronic Acids; D002712:Chlorides; D006859:Hydrogen; D001554:Benzene; D000181:Acrylonitrile