42. A DFT mechanistic study on gold(I)-catalyzed cascade reaction of aminaloalkyne involving Petasis-Ferrier cyclization

Shi, J.; Bi, S.;* Jiang, Y.-Y.; Liu, Y.; Ling, B.; Yuan, X.-A. J. Organometal. Chem. 2018, 864, 136–142. Download Link

Abstract: The reaction mechanism of gold(I)-catalyzed cascade reaction of aminaloalkynes involving PetasisFerrier arrangement was studied with the aid of density functional theory calculations. Our study showed that two mechanisms proposed by the Patil group and by us are possible. With the substrate bearing a -C≡C-H component the mechanism by us is preferred in which the reaction undergoes first a Petasis-Ferrier rearrangement. With the substrate bearing a -C≡C-Ar component the mechanism by the Patil group is preferred in which the reaction undergoes first a protodeauration step. In summary, both reaction mechanisms are related and reaction substrate governs which pathway is followed.