Room-Temperature Negishi Reaction of Trisubstituted Vinyl Phosphates for the Synthesis of Tetrasubstituted Alkenes.

The present study investigated the ability of bromovinyl phosphates to react with organozinc reagents at room temperature during palladium-catalyzed reactions. It was determined that both the bromine atom and the phosphate group were successfully substituted by means of the reaction with the organozinc reagents, thereby allowing for the synthesis of cyclic and acyclic tetrasubstituted double bonds. The low stability of the organozinc compounds in an acidic environment was exploited to accomplish the synthesis of alkenes using a one-pot, two-step experimental setup.