title: BF3·Et2O-promoted cleavage of the Csp-Csp2 bond of 2-propynolphenols/anilines: route to C2-alkenylated benzoxazoles and benzimidazoles.
abstract: A novel BF3·Et2O-promoted tandem reaction of easily prepared 2-propynolphenols/anilines and trimethylsilyl azide is developed to give C2-alkenylated benzoxazoles and benzimidazoles in moderate to good yields. Most reactions could be accomplished in 30 min at room temperature. This tandem process involves a Csp-Csp2 bond cleavage and a C-N bond formation. Moreover, both tertiary and secondary propargylic alcohols with diverse functional groups were tolerated under the mild conditions.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou 730000, P.R. China.
authors.forename: Xian-Rong
authors.initials: XR
authors.lastname: Song
authors.forename: Yi-Feng
authors.initials: YF
authors.lastname: Qiu
authors.forename: Bo
authors.initials: B
authors.lastname: Song
authors.forename: Xin-Hua
authors.initials: XH
authors.lastname: Hao
authors.forename: Ya-Ping
authors.initials: YP
authors.lastname: Han
authors.forename: Pin
authors.initials: P
authors.lastname: Gao
authors.forename: Xue-Yuan
authors.initials: XY
authors.lastname: Liu
authors.forename: Yong-Min
authors.initials: YM
authors.lastname: Liang
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D001583:Benzoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D001880:Boranes / Q000737:chemistry*; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*
chemical_list: D000814:Aniline Compounds; D001562:Benzimidazoles; D001583:Benzoxazoles; D001880:Boranes; D010636:Phenols; C101707:boron trifluoride etherate; C023650:aniline