Computational exploration for possible reaction pathways, regioselectivity, and influence of substrate in gold-catalyzed cycloaddition of cyanamides with enynamides.

ABSTRACT: The current work focuses on the DFT calculation of the rational mechanism and catalytic activity of the gold(i)-catalyzed isotetradehydro-Diels-Alder cycloaddition of cyanamides and enamides to substituted 2,6-diaminopyridines. IPrAuCl is used as a model catalyst to catalyze cyanamide and enynamide reactants with different substituents in DCM as a research system. DFT data indicates that the catalytic cycle starts from the triple bond coordination between the catalyst's gold cation and the enamide to obtain the gold π-complex, and the cyanamide attacks the alkynyl carbon atom from different directions to generate two reaction channels of five-membered and six-membered heterocycles, respectively. The calculation results show that the 2,6-diaminopyridine compounds produced by this catalytic

SUBMITTER: Zhang X 

PROVIDER: S-EPMC9377310 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature