Synthesis of vinyl fluorides by ring-closing metathesis

The first ring-closing olefin metatheses of alkenyl α-fluoroacrylamides or acrylates incorporating a fluorinated double bond are reported. Several N-benzyl-N-alkenyl-α-fluoroacrylamides were cyclized in the presence of 2 mol % of Grubbs II catalyst at room temperature to form an unsaturated γ-lactam, and at 80 °C to form the corresponding δ-lactams bearing a fluoro vinyl moiety. At elevated temperature, cyclization of an N-methallyl 2-fluoroacrylamide to form a fluorinated, tetrasubstituted double bond was achieved. Similarly, 3-fluorocoumarin was prepared from (2-vinylphenyl)-α-fluoroacrylate.