Stereoretentive and regioselective selenium-catalyzed intermolecular propargylic C-H amination of alkynes.

ABSTRACT: Herein we report an intermolecular propargylic C-H amination of alkynes. This reaction is operationally convenient and requires no transition metal catalysts or additives. Terminal, silyl, and internal alkynes bearing a wide range of functional groups can be aminated in high yields. The regioselectivity of amination for unsymmetrical internal alkynes is strongly influenced by substitution pattern (tertiary > secondary > primary) and by relatively remote heteroatomic substituents. We demonstrate that amination of alkynes bearing α-stereocenters occurs with retention of configuration at the newly-formed C-N bond. Competition experiments between alkynes, kinetic isotope effects, and DFT calculations are performed to confirm the mechanistic hypothesis that initial ene reaction of a selenium bi

SUBMITTER: Maloney TP 

PROVIDER: S-EPMC8849008 | biostudies-literature | 2022 Feb

REPOSITORIES: biostudies-literature