Gold(I)-Catalyzed Reaction of Ferrocene and Propargylic Esters: Synthesis of Functionalized Ferrocene Derivatives

Abstract

The reaction of propargylic esters with ferrocene in the presence of gold catalysts provided ferrocene derivatives containing a functionalized vinyl moiety. This ferrocene C-H bond functionalization takes place with complete regio- and stereoselectivity. The reaction is proposed to proceed through an electrophilic substitution in which a vinylgold carbene intermediate arising from a 1,2-rearrangement of the starting propargylic ester would behave as the electrophilic counterpart.