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Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses

Several novel chiral N-heterocyclic carbene and phosphine ligands were prepared from (S)-BINOL. Moreover, their ligated Au complexes were also successfully synthesized and characterized by X-ray crystal diffraction. A weak gold-π interaction between the Au atom and the aromatic ring in these gold co...

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Detalles Bibliográficos
Autores principales: Sun, Yin-wei, Xu, Qin, Shi, Min
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3817475/
https://www.ncbi.nlm.nih.gov/pubmed/24204435
http://dx.doi.org/10.3762/bjoc.9.261
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author Sun, Yin-wei
Xu, Qin
Shi, Min
author_facet Sun, Yin-wei
Xu, Qin
Shi, Min
author_sort Sun, Yin-wei
collection PubMed
description Several novel chiral N-heterocyclic carbene and phosphine ligands were prepared from (S)-BINOL. Moreover, their ligated Au complexes were also successfully synthesized and characterized by X-ray crystal diffraction. A weak gold-π interaction between the Au atom and the aromatic ring in these gold complexes was identified. Furthermore, we confirmed the formation of a pair of diastereomeric isomers in NHC gold complexes bearing an axially chiral binaphthyl moiety derived from the hindered rotation around C–C and C–N bonds. In the asymmetric intramolecular hydroamination reaction most of these chiral Au(I) complexes showed good catalytic activities towards olefins tethered with a NHTs functional group to give the corresponding product in moderate yields and up to 29% ee.
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spelling pubmed-38174752013-11-07 Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses Sun, Yin-wei Xu, Qin Shi, Min Beilstein J Org Chem Full Research Paper Several novel chiral N-heterocyclic carbene and phosphine ligands were prepared from (S)-BINOL. Moreover, their ligated Au complexes were also successfully synthesized and characterized by X-ray crystal diffraction. A weak gold-π interaction between the Au atom and the aromatic ring in these gold complexes was identified. Furthermore, we confirmed the formation of a pair of diastereomeric isomers in NHC gold complexes bearing an axially chiral binaphthyl moiety derived from the hindered rotation around C–C and C–N bonds. In the asymmetric intramolecular hydroamination reaction most of these chiral Au(I) complexes showed good catalytic activities towards olefins tethered with a NHTs functional group to give the corresponding product in moderate yields and up to 29% ee. Beilstein-Institut 2013-10-28 /pmc/articles/PMC3817475/ /pubmed/24204435 http://dx.doi.org/10.3762/bjoc.9.261 Text en Copyright © 2013, Sun et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Sun, Yin-wei
Xu, Qin
Shi, Min
Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses
title Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses
title_full Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses
title_fullStr Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses
title_full_unstemmed Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses
title_short Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses
title_sort synthesis of axially chiral gold complexes and their applications in asymmetric catalyses
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3817475/
https://www.ncbi.nlm.nih.gov/pubmed/24204435
http://dx.doi.org/10.3762/bjoc.9.261
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