New Strategies in Carbene Transfer Catalysis

Catalytic carbene transfer reactions commonly rely on diazoalkanes as storable precursors to reactive transition metal-bound carbenes. A well-established limitation of these reagents is their poor stability in the absence of electron-withdrawing substituents. As a consequence, there are few catalytic processes that are amenable to the use of non-stabilized carbene equivalents and many of these are impractical for preparative-scale applications.
In this seminar, I will outline a catalytic strategy for the generation of transition metal carbenoids from the reductive activation of readily available and indefinitely stable gem-dihaloalkanes. These reactions share mechanistic features with catalytic cross-couplings and rely on carbon - halogen oxidative addition as an activation mode. Nickel and cobalt-catalyzed transfer reactions of methylene, isopropylidene and vinylidene will be described.

Speaker: Chris Uyeda, Purdue