Dual H-bond activation of NHC-Au(i)-Cl complexes with amide functionalized side-arms assisted by H-bond donor substrates or acid additives

Otto Seppänen; Santeri Aikonen; Mikko Muuronen; Carla Alamillo-Ferrer; Jordi Burés; Juho Helaja

doi:10.1039/d0cc05999d

Dual H-bond activation of NHC-Au(i)-Cl complexes with amide functionalized side-arms assisted by H-bond donor substrates or acid additives

Chem Commun (Camb). 2020 Dec 4;56(93):14697-14700. doi: 10.1039/d0cc05999d. Epub 2020 Nov 10.

Authors

Otto Seppänen¹, Santeri Aikonen, Mikko Muuronen, Carla Alamillo-Ferrer, Jordi Burés, Juho Helaja

Affiliation

¹ Department of Chemistry, University of Helsinki, A. I. Virtasen aukio 1, P.O. Box 55, 00014, Finland. juho.helaja@helsinki.

PMID: 33169740
DOI: 10.1039/d0cc05999d

Abstract

Novel approach with amide-tethered H-bond donor NHC ligands enabled Au(i)-catalysis via H-bonding. The plain NHC-Au(i)-Cl complex catalysed conversions of terminal N-propynamides to oxazolines, and enyne cycloisomerization with an acid additive, in DCM at RT. DFT calculations enlightened the function of the side-arm in the activation.