Direct transformation of arylpropynes to acrylamides via a three-step tandem reaction.
A novel and metal-free acrylamides formation between arylpropynes and hydroxylamine hydrochloride through sp(3) C-H and C-C bond cleavage has been achieved with DDQ as an oxidant. The mechanistic study shows that the acrylamides are formed through a three-step tandem sequence, including cross-dehydrogenative-coupling (CDC) reaction, aza-Meyer-Schuster rearrangement and Beckmann rearrangement.
Department of Chemistry, Tongji University, Shanghai 200092, P. R. China.
Jun
J
Qiu
Ronghua
R
Zhang
D000480:Alkynes / Q000737:chemistry*; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D019811:Hydroxylamine / Q000737:chemistry; D015394:Molecular Structure
D000480:Alkynes; D000577:Amides; C022030:methylacetylene; D019811:Hydroxylamine