title: Lewis acid controlled regioselectivity in styrene hydrocyanation.
abstract: According to present knowledge, the Ni-catalyzed hydrocyanation of styrene leads predominantly to the branched product 2-phenylpropionitrile (98 %). We observed a dramatic inversion of the regioselectivity upon addition of a Lewis acid. Up to 83 % of the linear product 3-phenylpropionitrile was obtained by applying phosphite ligands in the presence of AlCl(3). The mechanism of the Ni-catalyzed reaction and the influence of additional Lewis acids have been investigated by means of deuterium labeling experiments, NMR studies, and DFT calculations. Furthermore, the behavior of different Lewis acids, such as CuCN, could be rationalized and predicted by DFT calculations.
authors.affiliation: Schuit Institute of Catalysis, Laboratory for Inorganic Chemistry and Catalysis, Eindhoven University of Technology, 5600 MB Eindhoven, The Netherlands.
authors.forename: Laura
authors.initials: L
authors.lastname: Bini
authors.forename: Evgeny A
authors.initials: EA
authors.lastname: Pidko
authors.forename: Christian
authors.initials: C
authors.lastname: Müller
authors.forename: Rutger A
authors.initials: RA
authors.lastname: van Santen
authors.forename: Dieter
authors.initials: D
authors.lastname: Vogt