"N-Heterocyclic Carbene Catalyzed Carba-, Sulfa-, and Phospha-Michael Additions with NHC·CO2 Adducts as Precatalysts"

Morgan Hans, Lionel Delaude, Jean Rodriguez, and Yoann Coquerel

journal cover
          source: Journal of Organic Chemistry
            year: 2014
          volume: 79
      first page: 2758
       last page: 2764
             doi: 10.1021/jo500108a

graphical abstract

Abstract: N-heterocyclic carbene catalyzed Michael additions have been revisited with 1,3-dialkyl- or 1,3-diarylimidazol(in)ium-2-carboxylates, that is NHC·CO2 adducts, as the source of the free NHC catalysts in solution. Using these precatalysts, a number of efficient carba-, sulfa-, and phospha-Michael additions were achieved very conveniently, without the need for an external strong base to generate the NHC by deprotonation of an azolium salt. To further expand the scope of the procedure, some NHC-catalyzed sulfa-Michael/aldol organocascades were also investigated.

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