Synthesis and use of bench-stable precatalysts with heck-type activation and progress towards the continuous-flow synthesis of atorvastatin

Abstract

[color illustrations] We introduce a new class of bench-stable N-heterocyclic carbene nickel precatalysts for homogeneous nickel-catalysis. The nickel(II) complexes are readily activated to Ni⁰ in situ under mild conditions, via a proposed Heck-type mechanism. The precatalysts are able to facilitate carbonyl-ene, hydroalkenylation, and amination reactions. [color illustrations] Herein, we report the synthesis and characterization of a new class of air- and moisture-stable triphenylphosphine nickel(II) precatalysts, which activate through a Heck-type mechanism. The activity of these precatalysts is demonstrated with a carbonyl-ene coupling reaction.