Lewis Acid Controlled Regioselectivity in Styrene Hydrocyanation

Laura Bini, Evgeny A. Pidko, Christian Muller, Rutger A. van Santen, Dieter Vogt

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)8768-8778
Number of pages11
JournalChemistry - A European Journal
Volume15
Issue number35
DOIs
Publication statusPublished - 2009

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