Axially chiral bis-1,2,3-Triazol-4-ylidene–Ag(I)-MIC and, bis-Au(I)-MIC complexes of (R)-BINOL and (-)-Menthol scaffold: Synthesis, structure, and characterizations

Manoj Kumar Gangwar; Ray J. Butcher

doi:10.1016/j.jorganchem.2020.121626

Axially chiral bis-1,2,3-Triazol-4-ylidene–Ag(I)-MIC and, bis-Au(I)-MIC complexes of (R)-BINOL and (-)-Menthol scaffold: Synthesis, structure, and characterizations

Manoj Kumar Gangwar, Ray J. Butcher

Physical Sciences and Engineering

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

4 Scopus citations

Abstract

Herein, we report the novel axially chiral bis-Ag(I)-MIC and, bis-Au(I)-MIC complexes bearing axially chiral bis-1,2,3-triazolium-derived mesoionic carbene (tz-MIC) ligands were synthesized. The enantiopure R-BINOL was employed as a basic unit to synthesize a axially chiral bis-1,2,3-triazolium-derived mesoionic carbene (tz-MIC) ligands (1–2)a. In particular, the axially chiral bis-1,2,3-triazolium-derived mesoionic carbene (tz-MIC) ligands (1–2)a, were obtained from the reaction of corresponding bis-1,2,3-triazole ligand precursor with methyl and ethyl iodide in 82−90% yields. Novel axially chiral bis-Ag(I)-MIC complexes (1 − 2)b, were prepared by the treatment of corresponding axially chiral bis-1,2,3-triazolium-derived mesoionic carbene (tz-MIC) iodide salts, (1 − 2)a, with Ag2O via in-situ deprotonation method in 69−86% yields. Novel axially chiral bis-Au(I)-MIC complex-2c was synthesized from their respective novel axially chiral bis-Ag(I)-MIC complex-2b, using transmetallation reaction with (SMe2)AuCl in 70% yield. All these novel axially chiral bis-Ag(I)-MIC and bis-Au(I)-MIC complexes were isolated for the first time and structurally characterized by 1H NMR and 13C{1H}-NMR spectroscopy, FT-IR spectroscopy, mass spectrometry, elemental analysis, specific optical rotation and, single crystal X-ray crystallography.

Original language	English (US)
Pages (from-to)	121626
Journal	Journal of Organometallic Chemistry
Volume	932
DOIs	https://doi.org/10.1016/j.jorganchem.2020.121626
State	Published - Nov 26 2020

Bibliographical note

KAUST Repository Item: Exported on 2020-12-22
Acknowledgements: MKG thanks to the Council of Scientific and Industrial Research (CSIR File No: 09/087(0663)/2010-EMR-I), New Delhi, for financial support of this research. The author gratefully acknowledge to the Single Crystal X-ray Diffraction Facility, Department of Chemistry IIT Bombay, India. The author also thanks to Professor P. Ghosh from Department of Chemistry, IIT Bombay, for his technical support. The author thanks to Professor Raymond John Butcher for solving the Single Crystal X-ray structures. The author gratefully acknowledge to CSIR, New Delhi for research fellowship.

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10.1016/j.jorganchem.2020.121626

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@article{096c7c30b0c744bdae2a61be65858d9e,

title = "Axially chiral bis-1,2,3-Triazol-4-ylidene–Ag(I)-MIC and, bis-Au(I)-MIC complexes of (R)-BINOL and (-)-Menthol scaffold: Synthesis, structure, and characterizations",

abstract = "Herein, we report the novel axially chiral bis-Ag(I)-MIC and, bis-Au(I)-MIC complexes bearing axially chiral bis-1,2,3-triazolium-derived mesoionic carbene (tz-MIC) ligands were synthesized. The enantiopure R-BINOL was employed as a basic unit to synthesize a axially chiral bis-1,2,3-triazolium-derived mesoionic carbene (tz-MIC) ligands (1–2)a. In particular, the axially chiral bis-1,2,3-triazolium-derived mesoionic carbene (tz-MIC) ligands (1–2)a, were obtained from the reaction of corresponding bis-1,2,3-triazole ligand precursor with methyl and ethyl iodide in 82−90% yields. Novel axially chiral bis-Ag(I)-MIC complexes (1 − 2)b, were prepared by the treatment of corresponding axially chiral bis-1,2,3-triazolium-derived mesoionic carbene (tz-MIC) iodide salts, (1 − 2)a, with Ag2O via in-situ deprotonation method in 69−86% yields. Novel axially chiral bis-Au(I)-MIC complex-2c was synthesized from their respective novel axially chiral bis-Ag(I)-MIC complex-2b, using transmetallation reaction with (SMe2)AuCl in 70% yield. All these novel axially chiral bis-Ag(I)-MIC and bis-Au(I)-MIC complexes were isolated for the first time and structurally characterized by 1H NMR and 13C{1H}-NMR spectroscopy, FT-IR spectroscopy, mass spectrometry, elemental analysis, specific optical rotation and, single crystal X-ray crystallography.",

author = "Gangwar, {Manoj Kumar} and Butcher, {Ray J.}",

note = "KAUST Repository Item: Exported on 2020-12-22 Acknowledgements: MKG thanks to the Council of Scientific and Industrial Research (CSIR File No: 09/087(0663)/2010-EMR-I), New Delhi, for financial support of this research. The author gratefully acknowledge to the Single Crystal X-ray Diffraction Facility, Department of Chemistry IIT Bombay, India. The author also thanks to Professor P. Ghosh from Department of Chemistry, IIT Bombay, for his technical support. The author thanks to Professor Raymond John Butcher for solving the Single Crystal X-ray structures. The author gratefully acknowledge to CSIR, New Delhi for research fellowship.",

year = "2020",

month = nov,

day = "26",

doi = "10.1016/j.jorganchem.2020.121626",

language = "English (US)",

volume = "932",

pages = "121626",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier",

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TY - JOUR

T1 - Axially chiral bis-1,2,3-Triazol-4-ylidene–Ag(I)-MIC and, bis-Au(I)-MIC complexes of (R)-BINOL and (-)-Menthol scaffold: Synthesis, structure, and characterizations

AU - Gangwar, Manoj Kumar

AU - Butcher, Ray J.

N1 - KAUST Repository Item: Exported on 2020-12-22 Acknowledgements: MKG thanks to the Council of Scientific and Industrial Research (CSIR File No: 09/087(0663)/2010-EMR-I), New Delhi, for financial support of this research. The author gratefully acknowledge to the Single Crystal X-ray Diffraction Facility, Department of Chemistry IIT Bombay, India. The author also thanks to Professor P. Ghosh from Department of Chemistry, IIT Bombay, for his technical support. The author thanks to Professor Raymond John Butcher for solving the Single Crystal X-ray structures. The author gratefully acknowledge to CSIR, New Delhi for research fellowship.

PY - 2020/11/26

Y1 - 2020/11/26

N2 - Herein, we report the novel axially chiral bis-Ag(I)-MIC and, bis-Au(I)-MIC complexes bearing axially chiral bis-1,2,3-triazolium-derived mesoionic carbene (tz-MIC) ligands were synthesized. The enantiopure R-BINOL was employed as a basic unit to synthesize a axially chiral bis-1,2,3-triazolium-derived mesoionic carbene (tz-MIC) ligands (1–2)a. In particular, the axially chiral bis-1,2,3-triazolium-derived mesoionic carbene (tz-MIC) ligands (1–2)a, were obtained from the reaction of corresponding bis-1,2,3-triazole ligand precursor with methyl and ethyl iodide in 82−90% yields. Novel axially chiral bis-Ag(I)-MIC complexes (1 − 2)b, were prepared by the treatment of corresponding axially chiral bis-1,2,3-triazolium-derived mesoionic carbene (tz-MIC) iodide salts, (1 − 2)a, with Ag2O via in-situ deprotonation method in 69−86% yields. Novel axially chiral bis-Au(I)-MIC complex-2c was synthesized from their respective novel axially chiral bis-Ag(I)-MIC complex-2b, using transmetallation reaction with (SMe2)AuCl in 70% yield. All these novel axially chiral bis-Ag(I)-MIC and bis-Au(I)-MIC complexes were isolated for the first time and structurally characterized by 1H NMR and 13C{1H}-NMR spectroscopy, FT-IR spectroscopy, mass spectrometry, elemental analysis, specific optical rotation and, single crystal X-ray crystallography.

AB - Herein, we report the novel axially chiral bis-Ag(I)-MIC and, bis-Au(I)-MIC complexes bearing axially chiral bis-1,2,3-triazolium-derived mesoionic carbene (tz-MIC) ligands were synthesized. The enantiopure R-BINOL was employed as a basic unit to synthesize a axially chiral bis-1,2,3-triazolium-derived mesoionic carbene (tz-MIC) ligands (1–2)a. In particular, the axially chiral bis-1,2,3-triazolium-derived mesoionic carbene (tz-MIC) ligands (1–2)a, were obtained from the reaction of corresponding bis-1,2,3-triazole ligand precursor with methyl and ethyl iodide in 82−90% yields. Novel axially chiral bis-Ag(I)-MIC complexes (1 − 2)b, were prepared by the treatment of corresponding axially chiral bis-1,2,3-triazolium-derived mesoionic carbene (tz-MIC) iodide salts, (1 − 2)a, with Ag2O via in-situ deprotonation method in 69−86% yields. Novel axially chiral bis-Au(I)-MIC complex-2c was synthesized from their respective novel axially chiral bis-Ag(I)-MIC complex-2b, using transmetallation reaction with (SMe2)AuCl in 70% yield. All these novel axially chiral bis-Ag(I)-MIC and bis-Au(I)-MIC complexes were isolated for the first time and structurally characterized by 1H NMR and 13C{1H}-NMR spectroscopy, FT-IR spectroscopy, mass spectrometry, elemental analysis, specific optical rotation and, single crystal X-ray crystallography.

UR - http://hdl.handle.net/10754/666501

UR - https://linkinghub.elsevier.com/retrieve/pii/S0022328X20305295

UR - http://www.scopus.com/inward/record.url?scp=85097371748&partnerID=8YFLogxK

U2 - 10.1016/j.jorganchem.2020.121626

DO - 10.1016/j.jorganchem.2020.121626

M3 - Article

SN - 0022-328X

VL - 932

SP - 121626

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

ER -

Axially chiral bis-1,2,3-Triazol-4-ylidene–Ag(I)-MIC and, bis-Au(I)-MIC complexes of (R)-BINOL and (-)-Menthol scaffold: Synthesis, structure, and characterizations

Abstract

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CCDC 1044413: Experimental Crystal Structure Determination : (mu-4,4'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]bis{3-ethyl-1-[5-methyl-2-(propan-2-yl)cyclohexyl]-1H-1,2,3-triazol-5-ylidene})-dichloro-di-silver(i) acetonitrile unknown solvate

CCDC 1406311: Experimental Crystal Structure Determination : (mu-4,4'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]bis{3-ethyl-1-[5-methyl-2-(propan-2-yl)cyclohexyl]-1H-1,2,3-triazol-5-ylidene})-dichloro-di-gold(i)

Cite this

Axially chiral bis-1,2,3-Triazol-4-ylidene–Ag(I)-MIC and, bis-Au(I)-MIC complexes of (R)-BINOL and (-)-Menthol scaffold: Synthesis, structure, and characterizations

Abstract

Bibliographical note

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1044413: Experimental Crystal Structure Determination : (mu-4,4'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]bis{3-ethyl-1-[5-methyl-2-(propan-2-yl)cyclohexyl]-1H-1,2,3-triazol-5-ylidene})-dichloro-di-silver(i) acetonitrile unknown solvate

CCDC 1406311: Experimental Crystal Structure Determination : (mu-4,4'-[[1,1'-binaphthalene]-2,2'-diylbis(oxymethylene)]bis{3-ethyl-1-[5-methyl-2-(propan-2-yl)cyclohexyl]-1H-1,2,3-triazol-5-ylidene})-dichloro-di-gold(i)

Cite this