title: TMSCl-mediated synthesis of α,β-unsaturated amides via C-C bond cleavage and C-N bond formation of propargyl alcohols with trimethylsilyl azide.
abstract: A new method with high efficiency for the synthesis of α,β-unsaturated amides from the easily prepared propargyl alcohols and TMSN3 using TMSCl as an acid promoter is developed. A wide variety of α,β-unsaturated amides were produced in moderate to excellent yields. Mechanistic studies indicate that this transformation involves TMSCl-mediated allenylazide intermediate formation, C-C bond cleavage, and C-N bond formation. Significantly, this reaction shows good functional group compatibility and high regioselectivity, with a relatively short reaction time and inexpensive reagents.
authors: State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou 730000, People's Republic of China.
authors: Xian-Rong
authors: XR
authors: Song
authors: Bo
authors: B
authors: Song
authors: Yi-Feng
authors: YF
authors: Qiu
authors: Ya-Ping
authors: YP
authors: Han
authors: Zi-Hang
authors: ZH
authors: Qiu
authors: Xin-Hua
authors: XH
authors: Hao
authors: Xue-Yuan
authors: XY
authors: Liu
authors: Yong-Min
authors: YM
authors: Liang