Light-Induced Mechanistic Divergence in Gold(I) Catalysis: Revisiting the Reactivity of Diazonium Salts.

ABSTRACT: In a systematic study of the Au-catalyzed reaction of o-alkynylphenols with aryldiazonium salts, we find that essentially the same reaction conditions lead to a change in mechanism when a light source is applied. If the reaction is carried out at room temperature using a Au^I catalyst, the diazonium salt undergoes electrophilic deauration of a vinyl Au^I intermediate and provides access to substituted azobenzofurans. If the reaction mixture is irradiated with blue LED light, C-C bond formation due to N₂ -extrusion from the diazonium salt is realized selectively, using the same starting materials without the need for an additional photo(redox) catalyst under aerobic conditions. We report a series of experiments demonstrating that the same vinyl Au^I

SUBMITTER: Taschinski S 

PROVIDER: S-EPMC6899485 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature