N-heterocyclic carbenes (NHCs) are important ligands for various catalytic reactions. Recently, acyclic diaminocarbenes (ADCs) have emerged as interesting alternatives, as they show unique electronic and steric profiles owing to the larger N-C-N carbene bond angles and conformational flexibility. However, the synthesis of such acyclic carbenes is generally more challenging, and most of the known ADCs were less bulky than commonly used NHCs. Our laboratory has developed highly hindered N,N'-dialkyl-N,N'-diaryl ADCs of which steric demands are comparable to those of bulky NHCs. Interestingly, the bulky diaryl ADCs demonstrate unique ligand properties very different from bulky NHC congeners. During this presentation, novel synthetic methods for acyclic carbene generation, applications of acyclic carbenes in catalysis, and recent study on acyclic aminooxycarbenes will be discussed in detail.

Development of acyclic carbene ligands: Synthesis and application in catalysis

244th National Meeting (2012)

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