Functionalization of Internal Arylalkynes with Nitrosylsulfuric Acid: Access to Arylated 1,2-Diketones and 1,3-Oxazoles
Abstract
Nitrosylsulfuric acid was found to be an efficient oxidant for converting internal arylalkynes into their corresponding benzils. This 1,2-dicarbonylation proceeds under mild conditions at ambient temperature in nitromethane in the presence of catalytic amounts of iodine, affording benzils in 30–99% yields. Replacing nitromethane with acetonitrile crucially influences the composition of the products, with the main reaction products being substituted 1,3-oxazoles. The mechanism of the transformations was investigated by experiments with H 2 18 O.
Fields of Study & Subjects
Oxidative Organic Chemistry Reactions
Catalytic Alkyne Reactions
Chemical Synthesis and Reactions
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Volume
- 91
- Issue
- 8
- Pages
- 3047–3056
- Publication date
- 16 February 2026
- Language
- EN