Isotope effects and the nature of stereo- and regioselectivity in hydroaminations of vinylarenes catalyzed by palladium(ii)-diphosphine complexes. Academic Article uri icon

abstract

  • [reaction: see text] The hydroamination of styrene with aniline catalyzed by phosphine-ligated palladium triflates exhibits a substantial (13)C isotope effect at the benzylic carbon. This supports rate-determining nucleophilic attack of amine on a eta(3)-phenethyl palladium complex. Deuterium exchange observations and predicted isotope effects based on DFT calculations support this mechanism. Selectivity in these reactions is determined by the facility of palladium displacement after reversible hydropalladation of the alkene.

author list (cited authors)

  • Vo, L. K., & Singleton, D. A

citation count

  • 44

complete list of authors

  • Vo, Loan K||Singleton, Daniel A

publication date

  • January 1, 2004 11:11 AM