Metal-free hydroarylation of the side chain carbon-carbon double bond of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles in triflic acid.

ABSTRACT: The metal-free reaction of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles with arenes in neat triflic acid (TfOH, CF₃SO₃H), both under thermal and microwave conditions, leads to 5-(2,2-diarylethyl)-3-aryl-1,2,4-oxadiazoles. The products are formed through the regioselective hydroarylation of the side chain carbon-carbon double bond of the starting oxadiazoles in yields up to 97%. According to NMR data and DFT calculations, N⁴,C-diprotonated forms of oxadiazoles are the electrophilic intermediates in this reaction.

SUBMITTER: Zalivatskaya AS 

PROVIDER: S-EPMC5433146 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature