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

Publication date: Available online 10 March 2018 Source:Journal of Organometallic Chemistry Author(s): Jing Shi, Siwei Bi, Yuan-Ye Jiang, Yuxia Liu, Baoping Ling, Xiang-Ai Yuan The reaction mechanism of gold(I)-catalyzed cascade reaction of aminaloalkynes involving Petasis-Ferrier 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. Graphical abstract

Source: Journal of Organometallic Chemistry - March 10, 2018 Category: Chemistry Source Type: research