Deprotonation of carbene precursor salts with strong bases has proved a reliable route to almost all stable carbenes:
Imidazol-2-ylidenes and dihydroimidazol-2-ylidenes, such IMes, have been prepared by the deprotonation of the respective imidazolium and dihydroimidazolium salts. The acyclic carbenes and the tetrahydropyrimidinyl based carbenes were prepared by deprotonation using strong homogeneous bases.
Several bases and reaction conditions have been employed with varying success. The degree of success has been principally dependent on the nature of the precursor being deprotonated. The major drawback with this method of preparation is the problem of isolation of the free carbene from the metals ions used in their preparation.