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BF3·OEt2-Promoted Propargyl Alcohol Rearrangement/[1,5]-Hydride Transfer/Cyclization Cascade Affording
Shuang Zhao1, Xiaoyang Wang1, Pengfei Wang1
1Tianjin Key Laboratory of Molecular Optoelectronic Science, Department of Chemistry, School of Science , Tianjin University , Tianjin 300072 , P. R. China.
Abstract:
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 the formation of ketones (via [1,3]-hydroxyl shift) or alkenyl fluorides which are products of formal trans-carbofluorination of internal alkynes. This method provides a rapid access to diverse heterocycles in moderate to excellent yields.
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