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

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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,

‡^a Santeri Aikonen,

‡^a Mikko Muuronen,§^a Carla Alamillo-Ferrer,^b Jordi Burés

^b and Juho Helaja

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, University of Helsinki, A. I. Virtasen aukio 1, P.O. Box 55, Finland
E-mail: juho.helaja@helsinki

^b The University of Manchester, School of Chemistry, Oxford Road, M13 9PL Manchester, UK

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.

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DOI: https://doi.org/10.1039/D0CC05999D
Article type: Communication
Submitted: 05 Sep 2020
Accepted: 03 Nov 2020
First published: 03 Nov 2020
This article is Open Access

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Chem. Commun., 2020,56, 14697-14700

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

O. Seppänen, S. Aikonen, M. Muuronen, C. Alamillo-Ferrer, J. Burés and J. Helaja, Chem. Commun., 2020, 56, 14697 DOI: 10.1039/D0CC05999D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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Chemical Communications

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

Abstract

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

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