Lewis Acid Controlled Regioselectivity in Styrene Hydrocyanation |
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| Authors: | Laura Bini Evgeny A Pidko Dr Christian Müller Dr Rutger A van Santen Prof Dr Dieter Vogt Prof Dr |
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| Institution: | Schuit Institute of Catalysis, Laboratory for Inorganic Chemistry and Catalysis, Eindhoven University of Technology, 5600 MB Eindhoven (The Netherlands), Fax: (+31)?40‐2472730 |
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| 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 AlCl3. 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. |
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| Keywords: | homogeneous catalysis hydrocyanation Lewis acids P ligands regioselectivity |
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