Chiral N-Heterocyclic Carbene Gold Complexes: Synthesis, Properties, and Application in Asymmetric Catalysis

Banerjee, Dipshikha; Buzas, Andréa Krisztina; Besnard, Céline; Kundig, Ernst Peter

doi:10.1021/om300917m

Scientific article

English

Chiral N-Heterocyclic Carbene Gold Complexes: Synthesis, Properties, and Application in Asymmetric Catalysis

Contributors

Banerjee, Dipshikha; Buzas, Andréa Krisztina; Besnard, Céline; Kundig, Ernst Peter

Published in

Organometallics, vol. 31, no. 23, p. 8348-8354

Publication date

2012

Abstract

Nine new N-heterocyclic carbene gold chloride complexes (10–18) were synthesized starting from bulky chiral imidazolium salts (1–9) developed in this laboratory. Full characterization of all complexes, including the X-ray structures of gold(I)(1,3-bis((S)-1-(2-methoxyphenyl)-2,2-dimethylpropyl)-1H-imidazol-2(3H)-ylidene) chloride (13) and gold(I)(1,3-bis((S)-2,2-dimethyl-1-(naphthalen-1-yl)propyl)-1H-imidazol-2(3H)-ylidene) chloride (16), is reported. The complexes 10–18 were applied in the methoxycyclization of 1,6-enynes using AgNTf2 as an additive. Synthesis of the N-heterocyclic carbene gold triflimidate (19) was achieved by treating complex 12 with AgNTf2. The complex gold(I)(1,3-bis((R)-1-(2-methoxyphenyl)-2,2-dimethylpropyl)imidazolidin-2-ylidene)(1,1,1-trifluoro-N-(trifluoromethylsulfonyl)methylsulfonamido) (19) was isolated and spectroscopically and structurally (X-ray) characterized.

UNIGE affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

BANERJEE, Dipshikha et al. Chiral N-Heterocyclic Carbene Gold Complexes: Synthesis, Properties, and Application in Asymmetric Catalysis. In: Organometallics, 2012, vol. 31, n° 23, p. 8348–8354. doi: 10.1021/om300917m

Article (Published version)

Identifiers

PID : unige:24435
DOI : 10.1021/om300917m

Journal ISSN

0276-7333

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10/12/2012 09:34:00

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10/12/2012 09:34:00

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14/03/2023 17:46:52

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14/03/2023 17:46:52

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30/10/2024 08:01:58

Chiral N-Heterocyclic Carbene Gold Complexes: Synthesis, Properties, and Application in Asymmetric Catalysis

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Published in

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Abstract

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Citation (ISO format)

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Creation

First validation

Update

Status update

Last indexation