Stereoselective Generation of (<i>E</i>)- and (<i>Z</i>)-2-Fluoroalkylidene-Type Carbenoids from (2-Fluoro-1-alkenyl)iodonium Salts and Their Application for Stereoselective Synthesis of Fluoroalkenes

Abstract

Alkylidene-type carbenoids, generated from (Z)- or (E)-(2-fluoro-1-alkenyl)iodonium salts by treatment with LDA, reacted with trialkylboranes to give (E)- or (Z)-(fluoroalkenyl)boranes stereoselectively. The resulting (fluoroalkenyl)borane can be used for the selective synthesis of (E)- or (Z)-fluoroalkenes, (E)- or (Z)-fluoroiodoalkenes, and alpha-fluoroketones. [reaction: see text]