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

Otto Seppänen, Santeri Aikonen, Mikko Muuronen, Carla Alamillo-ferrer, Jordi Burés, Juho Helaja

Organic Chemistry Group

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	14697-14700
Journal	Chemical Communications
Volume	56
Issue number	93
Early online date	3 Nov 2020
DOIs	https://doi.org/10.1039/D0CC05999D
Publication status	E-pub ahead of print - 3 Nov 2020

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10.1039/D0CC05999DLicence: CC BY

JB EPSRC NIA Nov18
Bures, J. (PI)
1/10/18 → 30/09/20
Project: Research

Cite this

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title = "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 = "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.",

author = "Otto Sepp{\"a}nen and Santeri Aikonen and Mikko Muuronen and Carla Alamillo-ferrer and Jordi Bur{\'e}s and Juho Helaja",

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doi = "10.1039/D0CC05999D",

language = "English",

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T1 - Dual H-bond activation of NHC–Au(I)–Cl complexes with amide functionalized side-arms assisted by H-bond donor substrates or acid additives

AU - Seppänen, Otto

AU - Aikonen, Santeri

AU - Muuronen, Mikko

AU - Alamillo-ferrer, Carla

AU - Burés, Jordi

AU - Helaja, Juho

PY - 2020/11/3

Y1 - 2020/11/3

N2 - 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.

AB - 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.

U2 - 10.1039/D0CC05999D

DO - 10.1039/D0CC05999D

M3 - Article

SN - 1359-7345

VL - 56

SP - 14697

EP - 14700

JO - Chemical Communications

JF - Chemical Communications

IS - 93

ER -

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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JB EPSRC NIA Nov18

Cite this