Single–carbon atom transfer to α,β-unsaturated amides from N-heterocyclic carbenes
Miharu Kamitani, Bunta Nakayasu, Hayato Fujimoto, Kosuke Yasui, Takuya Kodama, Mamoru Tobisu
Abstract
Single-carbon atom transfer reactions are lacking in organic synthesis, partly because of the absence of atomic carbon sources under standard solution-phase conditions. We report here that N-heterocyclic carbenes can serve as atomic carbon donors through the loss of a 1,2-diimine moiety. This strategy is applicable to single-carbon atom transfer to α,β-unsaturated amides, which can be converted into homologated γ-lactams through the formation of four single bonds to one carbon center in one operation.
Topics & Concepts
MoietyCarbon atomCarbon fibersChemistryAtom (system on chip)Carbon chainOrganic chemistryRing (chemistry)Materials scienceEmbedded systemComputer scienceComposite materialComposite numberAsymmetric Hydrogenation and CatalysisCatalytic Cross-Coupling ReactionsN-Heterocyclic Carbenes in Organic and Inorganic Chemistry