Ring-opening reactions of nonactivated aziridines catalyzed by tris(pentafluorophenyl)borane.
The ring-opening reactions of nonactivated aziridines with amine nucleophiles are efficiently catalyzed by tris(pentafluorophenyl)borane leading to derivatives of trans-1,2-diamines in high yields. A mechanistic investigation of the reaction suggests that in situ formed [(C(6)F(5))(3)B(OH(2))].H(2)O catalyzes the opening through a Brønsted acid manifold.
Watson
Iain D G
ID
Davenport Research Laboratories, Department of Chemistry, The University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
Yudin
Andrei K
AK