Chiral Tricyclic 1,2,3-Triazol-3-Ylidene–Pd(II) Complexes of Cyclohexene Oxide Scaffold: Synthesis, Structure, and Characterizations

22 Pages Posted: 15 Sep 2020

See all articles by manoj kumar gangwar

manoj kumar gangwar

affiliation not provided to SSRN

Ray J. Butcher

Howard University

Abstract

We herein report the two novel well-defined palladium(II) complexes 1(b−c), of the chiral N-fused tricyclic 1,2,3-triazolium-derived mesoionic carbenes (MIC) ligand 1a. The chiral tricyclic PEPPSI type complex namely, trans-{2-methyl-(5aS,9aS)-5a,6,7,8,9,9a-hexahydro-4H-benzo[b][1,2,3]triazolo[1,5-d][1,4]oxazin-3-ylidene}PdI2(pyridine)} (1b), and the chiral tricyclic bis(tz-MIC)-palladium complex namely, {2-methyl-(5aS,9aS)-5a,6,7,8,9,9a-hexahydro-4H-benzo[b][1,2,3]triazolo[1,5-d][1,4]oxazinium-3-ylidene}2PdCl2} (1c). The chiral tricyclic (tz-MIC)PdI2(pyridine) type PEPPSI complex (1b) was obtained by direct reaction of the corresponding chiral tricyclic 1,2,3-triazolium-derived mesoionic carbenes (MIC) ligand 1a, by treatment with PdCl2 in the presence of K2CO3 as a base in pyridine in 87% yield. (Scheme 1). The chiral tricyclic 1,2,3-triazolium iodide salt (1a) was converted to its in-situ silver analogue by reaction with Ag2O and then subsequently upon treatment with (COD)PdCl2 to produce the chiral tricyclic (tz-MIC)2PdCl2 type palladium complex (1c). All these palladium 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 and single crystal X-ray crystallography.

Keywords: Palladium, chiral N-fused tricyclic 1, 2, 3-triazolium-derived mesoionic carbene (MIC) ligand, bis(tz-MIC)-palladium complexes and PEPPSI type complexes (pyridine-enhanced pre-catalyst preparation stabilization and initiation), pseudomonas cepacia lipase enzyme, Cyclohexene oxide

Suggested Citation

gangwar, manoj kumar and Butcher, Ray J., Chiral Tricyclic 1,2,3-Triazol-3-Ylidene–Pd(II) Complexes of Cyclohexene Oxide Scaffold: Synthesis, Structure, and Characterizations. Available at SSRN: https://ssrn.com/abstract=3690933

Manoj kumar Gangwar (Contact Author)

affiliation not provided to SSRN

No Address Available

Ray J. Butcher

Howard University

2400 Sixth Street, NW
Washington, DC 20059
United States

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