917604-46-7Relevant academic research and scientific papers
Continuous-Flow N-Heterocyclic Carbene Generation and Organocatalysis
Di Marco, Lorenzo,Hans, Morgan,Delaude, Lionel,Monbaliu, Jean-Christophe M.
, p. 4508 - 4514 (2016)
Two methods were assessed for the generation of common N-heterocyclic carbenes (NHCs) from stable imidazol(in)ium precursors using convenient and straightforward continuous-flow setups with either a heterogeneous inorganic base (Cs2CO3 or K3PO4) or a homogeneous organic base (KN(SiMe3)2). In-line quenching with carbon disulfide revealed that the homogeneous strategy was most efficient for the preparation of a small library of NHCs. The generation of free nucleophilic carbenes was next telescoped with two benchmark NHC-catalyzed reactions; namely, the transesterification of vinyl acetate with benzyl alcohol and the amidation of N-Boc-glycine methyl ester with ethanolamine. Both organocatalytic transformations proceeded with total conversion and excellent yields were achieved after extraction, showcasing the first examples of continuous-flow organocatalysis with NHCs.
Assessing the potential of zwitterionic NHOCS2 adducts for probing the stereoelectronic parameters of N-heterocyclic carbenes
Delaude, Lionel,Demonceau, Albert,Wouters, Johan
experimental part, p. 1882 - 1891 (2009/10/30)
Five imidazol(in)ium-2-dithiocarboxylates bearing cyclo-hexyl, mesityl, or 2,6-diisopropylphenyl substituents on their nitrogen atoms were prepared from the corresponding N-heterocyclic carbenes (NHCs) by reaction with carbon disul-fide. They were charact
