Synthesis and Structural Characterization of N-Heterocyclic Carbene Complexes of Silver(I) and Rhodium(I) from Caffeine

Aysegul Kascatan-Nebioglu; Matthew J. Panzner; Jered C. Garrison; Claire A. Tessier; Wiley J. Youngs

doi:10.1021/om030689r

Synthesis and Structural Characterization of N-Heterocyclic Carbene Complexes of Silver(I) and Rhodium(I) from Caffeine

Aysegul Kascatan-Nebioglu, Matthew J. Panzner, Jered C. Garrison, Claire A. Tessier, Wiley J. Youngs

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Abstract

The imidazolium cation 1,3,7,9-tetramethylxanthinium methyl sulfate (1a) is obtained by the reaction of caffeine with dimethyl sulfate. The anion exchange of la gives 1,3,7,9-tetramethylxanthinium hexafluorophosphate (1b). Ligand 1a reacts with Ag ₂O in water to yield an N-heterocyclic carbene (NHC) silver(I) complex (2a). Similarly, ligand 1b reacts with Ag ₂O in DMSO to yield NHC silver(I) complex 2b in high yield. A carbene transfer reaction of 2b with [Rh(COD)Cl]2 gives NHC Rh(I) complex 3. All compounds were characterized by ¹H NMR, ¹³C NMR, and mass spectrometry. The solid-state structures of 1b, 2b, and 3 were determined by X-ray crystallography.

Original language	English (US)
Pages (from-to)	1928-1931
Number of pages	4
Journal	Organometallics
Volume	23
Issue number	8
DOIs	https://doi.org/10.1021/om030689r
State	Published - Apr 12 2004
Externally published	Yes

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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@article{e3acf262e59644c3b6c40e49619055e8,

title = "Synthesis and Structural Characterization of N-Heterocyclic Carbene Complexes of Silver(I) and Rhodium(I) from Caffeine",

abstract = "The imidazolium cation 1,3,7,9-tetramethylxanthinium methyl sulfate (1a) is obtained by the reaction of caffeine with dimethyl sulfate. The anion exchange of la gives 1,3,7,9-tetramethylxanthinium hexafluorophosphate (1b). Ligand 1a reacts with Ag 2O in water to yield an N-heterocyclic carbene (NHC) silver(I) complex (2a). Similarly, ligand 1b reacts with Ag 2O in DMSO to yield NHC silver(I) complex 2b in high yield. A carbene transfer reaction of 2b with [Rh(COD)Cl]2 gives NHC Rh(I) complex 3. All compounds were characterized by 1H NMR, 13C NMR, and mass spectrometry. The solid-state structures of 1b, 2b, and 3 were determined by X-ray crystallography.",

author = "Aysegul Kascatan-Nebioglu and Panzner, {Matthew J.} and Garrison, {Jered C.} and Tessier, {Claire A.} and Youngs, {Wiley J.}",

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doi = "10.1021/om030689r",

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T1 - Synthesis and Structural Characterization of N-Heterocyclic Carbene Complexes of Silver(I) and Rhodium(I) from Caffeine

AU - Kascatan-Nebioglu, Aysegul

AU - Panzner, Matthew J.

AU - Garrison, Jered C.

AU - Tessier, Claire A.

AU - Youngs, Wiley J.

PY - 2004/4/12

Y1 - 2004/4/12

N2 - The imidazolium cation 1,3,7,9-tetramethylxanthinium methyl sulfate (1a) is obtained by the reaction of caffeine with dimethyl sulfate. The anion exchange of la gives 1,3,7,9-tetramethylxanthinium hexafluorophosphate (1b). Ligand 1a reacts with Ag 2O in water to yield an N-heterocyclic carbene (NHC) silver(I) complex (2a). Similarly, ligand 1b reacts with Ag 2O in DMSO to yield NHC silver(I) complex 2b in high yield. A carbene transfer reaction of 2b with [Rh(COD)Cl]2 gives NHC Rh(I) complex 3. All compounds were characterized by 1H NMR, 13C NMR, and mass spectrometry. The solid-state structures of 1b, 2b, and 3 were determined by X-ray crystallography.

AB - The imidazolium cation 1,3,7,9-tetramethylxanthinium methyl sulfate (1a) is obtained by the reaction of caffeine with dimethyl sulfate. The anion exchange of la gives 1,3,7,9-tetramethylxanthinium hexafluorophosphate (1b). Ligand 1a reacts with Ag 2O in water to yield an N-heterocyclic carbene (NHC) silver(I) complex (2a). Similarly, ligand 1b reacts with Ag 2O in DMSO to yield NHC silver(I) complex 2b in high yield. A carbene transfer reaction of 2b with [Rh(COD)Cl]2 gives NHC Rh(I) complex 3. All compounds were characterized by 1H NMR, 13C NMR, and mass spectrometry. The solid-state structures of 1b, 2b, and 3 were determined by X-ray crystallography.

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Synthesis and Structural Characterization of N-Heterocyclic Carbene Complexes of Silver(I) and Rhodium(I) from Caffeine

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