Insights into palladium-catalyzed cyanation of bromobenzene: additive effects on the rate-limiting step.
Kinetic studies using reaction calorimetry were conducted under synthetically relevant conditions to study the effect of additives in the cyanation of bromobenzene catalyzed by palladium complexes. This work demonstrates that the addition of a catalytic amount of ZnBr(2) facilitates the reaction with an elimination of the induction period observed without additive. This study afforded a qualitative assessment of the effect of water on the rate-limiting step and the apparent reaction order in bromobenzene.
Buono
Frederic G
FG
Process Research and Development, Bristol-Myers Squibb Pharmaceutical Research Institute, One Squibb Drive, New Brunswick, New Jersey 08903, USA. Frederic.Buono@bms.com
Chidambaram
Rama
R
Mueller
Richard H
RH
Waltermire
Robert E
RE
D001965:Bromides / Q000737:chemistry; D001969:Bromobenzenes / Q000737:chemistry*; D002384:Catalysis; D003486:Cyanides / Q000737:chemistry; D007700:Kinetics; D009570:Nitriles / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D014867:Water / Q000737:chemistry; D017967:Zinc Compounds / Q000737:chemistry
D001965:Bromides; D001969:Bromobenzenes; D003486:Cyanides; D009570:Nitriles; D009942:Organometallic Compounds; D017967:Zinc Compounds; D014867:Water; D010165:Palladium; C032036:bromobenzene; C093802:zinc bromide