BF3·OEt2-Promoted Propargyl Alcohol Rearrangement/[1,5]-Hydride Transfer/Cyclization Cascade Affording Tetrahydroquinolines

• DOI: 10.1021/acs.orglett.9b01153
• Publication Date: 2019-05-30T16:17:13Z
• Authors: Shuang Zhao; Xiaoyang Wang; Pengfei Wang; Guangwei Wang; Wentao Zhao; Xiangyang Tang; Minjie Guo
• Keywords: Propargyl; Propargyl alcohol; Triple bond

An efficient BF3·OEt2-mediated propargyl alcohol rearrangement/[1,5]-hydride transfer/cyclization cascade for the synthesis of tetrahydroquinoline derivatives has been described. The substituents adjacent to triple bonds play an important role in formation ketones (via [1,3]-hydroxyl shift) or alkenyl fluorides which are products formal trans-carbofluorination internal alkynes. This method provides a rapid access diverse heterocycles moderate excellent yields.