Direct intramolecular carbon(sp2)-nitrogen(sp2) reductive elimination from gold(iii)

Jong Hyun Kim, R. Tyler Mertens, Amal Agarwal, Sean Parkin, Gilles Berger, Samuel G. Awuah

Research output: Contribution to journalArticlepeer-review

17 Scopus citations


The reactivity of bidentate AuIII-Cl species, [(C^N)AuCl2], with a bisphosphine or carbon donor ligands results in reductive elimination. Combined experimental and computational investigations lead to the first evidence of a direct intramolecular C(sp2)-N(sp2) bond formation from a monomeric [(C^N)AuCl2] gold(iii) complex. We show that bidentate ligated Au(iii) systems bypass transmetallation to form C(sp2)-N(sp2) species and NHC-Au-Cl. Mechanistic investigations of the reported transformation reveal a ligand-induced reductive elimination via a key AuIII intermediate. Kinetic studies of the reaction support a second-order rate process.

Original languageEnglish
Pages (from-to)6273-6282
Number of pages10
JournalDalton Transactions
Issue number18
StatePublished - 2019

Bibliographical note

Funding Information:
We are grateful to the staff and facilities at the University of Kentucky that supported this work. This study made use of the NMR facility supported by NSF (CHE-9977388) and the UK X-ray facility with funds from the MRI program of the National Science Foundation (grants CHE-0319176 and CHE-1625732). Thanks to the staff of CIC, Boston University for running mass spectrometry samples. We thank Prof. Dong-Sheng Yang and Prof. John P. Selegue for helpful comments on kinetics and chemistry, respectively. G. B. thanks the ULB-VUB computing centre for providing high performance computing facilities and useful technical support.

Publisher Copyright:
© The Royal Society of Chemistry 2019.

ASJC Scopus subject areas

  • Inorganic Chemistry


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