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

January 1, 2020Chemical CommunicationsOpen Access

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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Key Points

To determine whether amide-tethered N-heterocyclic carbene ligands can activate gold(I) chloride complexes via hydrogen bonding without relying on traditional silver salts.
Synthesized amide-tethered hydrogen-bond donor NHC-Au(I)-Cl complexes.
Evaluated catalytic performance in converting terminal N-propynamides to oxazolines and performing enyne cycloisomerization with an acid additive at room temperature in dichloromethane.
Conducted density functional theory (DFT) calculations to determine the activation mechanism facilitated by the functionalized side-arm.
The unmodified NHC-Au(I)-Cl complex successfully catalyzed the cyclization of terminal N-propynamides to oxazolines at room temperature.
Enyne cycloisomerization was achieved under ambient conditions upon the addition of an acid promoter.
DFT calculations confirmed that secondary-sphere hydrogen bonding from the amide side-arms facilitates chloride displacement and substrate activation.

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Implication

Experimental study demonstrates dual hydrogen-bond activation of gold(I) chloride complexes via amide side-arms, indicating a viable route for mild catalytic cyclizations.

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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Seppänen et al. (2020) studied this question.

synapsesocial.com/papers/6a86f6aaa6ddb97d43d3c774 https://doi.org/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

Key Points

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Implication

Abstract

Discussion

Cite This Study

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

Key Points

Ask about this paper

Implication

Abstract

Discussion

Cite This Study

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