The stereospecific preparation of F-alkenyl cadmium reagents directly from F-alkenyl iodides and bromides and cadmium metal

Abstract

F -Alkenyl cadmium reagents can be readily prepared via the direct reaction of F -alkenyl iodides or bromides with cadmium powder in DMF at room temperature to 60°C. The reactions proceed with total retention of configuration, and subsequent functionalization processes also proceed with stereochemical control. The thermal stability of the cadmium reagents is excellent, and the bis reagent ( Z -CF 3CFCF) 2Cd was isolated (via distillation) as a DMF or triglyme solvate. This approach provides a facile, easily scaled up, stereospecific, one-pot procedure to these stable alkenyl synthetic reagents.