Generalization of the Copper to Late-Transition-Metal Transmetallation to Carbenes beyond N-Heterocyclic Carbenes

Yannick D Bidal; Orlando Santoro; Mohand Melaimi; David B Cordes; Alexandra M Z Slawin; Guy Bertrand; Catherine S J Cazin

doi:10.1002/chem.201601254

Generalization of the Copper to Late-Transition-Metal Transmetallation to Carbenes beyond N-Heterocyclic Carbenes

Chemistry. 2016 Jun 27;22(27):9404-9. doi: 10.1002/chem.201601254. Epub 2016 May 30.

Authors

Yannick D Bidal¹, Orlando Santoro¹, Mohand Melaimi², David B Cordes¹, Alexandra M Z Slawin¹, Guy Bertrand², Catherine S J Cazin³

Affiliations

¹ EaStCHEM School of Chemistry, University of St Andrews, St Andrews, KY16 9ST, UK.
² UCSD-CNRS Joint Research Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA, 92093-0358, USA.
³ EaStCHEM School of Chemistry, University of St Andrews, St Andrews, KY16 9ST, UK. ccazin@gmail.com.

PMID: 27238837
DOI: 10.1002/chem.201601254

Abstract

Carbene transition-metal complexes have become a prevalent family of catalysts enabling numerous organic transformations. Their facile synthetic access is a matter of great importance. To this end, the Cu(I) -NHC transfer methodology has emerged as a powerful alternative presenting attractive advantages over other methods. Herein, we report the remarkable ability of copper to transfer not only NHCs but also other types of carbenes such as abnormal NHCs (aNHCs), cyclic (alkyl)(amino)carbenes (CAACs), and mesoionic carbenes (MICs) to various transition metal precursors.

Keywords: CAAC; abnormal; carbene transfer; copper; n-heterocyclic carbene.