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Palladium complexes of a new type of N-heterocyclic carbene ligand derived from a tricyclic triazolooxazine framework

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Abstract

A new type of tricyclic triazolooxazine derived N-heterocyclic carbene precursors were developed by the alkylation reaction of a tricyclic triazolooxazine framework. In particular, the reaction of 5a,6,7,8,9,9a-hexahydro-4H-benzo[b][1,2,3]triazolo[1,5-d][1,4]oxazine with methyl iodide and ethyl iodide yielded the tricyclic triazolooxazine derived N-heterocyclic carbene precursors, (1−2)a, in 67 −84% yield. The tricyclic triazolooxazinium iodide salts, (1−2)a, underwent metallation in a straight forward manner upon treatment with PdCl2 in the presence of K2CO3 in pyridine to give the trans-{3-(R)-5a,6,7,8,9,9a-hexahydro-4H-benzo[b][1,2,3]triazolo[1,5-d][1,4]oxazin-4-ylidene} PdI2(pyridine) [R = Me (1b), Et (2b)] complexes in 23 −25% yield. The new tricyclic triazolooxazine derived N-heterocyclic carbene moiety, as stabilized upon binding to palladium in the (1−2)b complexes, was structurally characterized by the X-ray single crystal diffraction studies.

A new class of a tricyclic triazolooxazine derived N-heterocyclic carbene ligand has been developed by simple alkylation of a tricyclic triazolooxazine framework and the ligand has been stabilized by complexation with palladium in its (NHC)PdI2(pyridine) type complexes.

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Acknowledgements

We thank Department of Science and Technology (Grant No: SR/S1/IC-50/2011), New Delhi, for financial support of this research. We thank Professor R. Murugavel for the use of his Single Crystal X-ray Diffraction Facility established through a DAE-SRC Outstanding Investigator Award along with the Single Crystal X-ray Diffraction Facility, Department of Chemistry IIT Bombay, India, for the crystallographic characterization data. MKG thanks CSIR, New Delhi for research fellowship.

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  1. Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400 076, India

    MANOJ KUMAR GANGWAR, ALOK CH KALITA & PRASENJIT GHOSH

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  1. MANOJ KUMAR GANGWAR
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  2. ALOK CH KALITA
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  3. PRASENJIT GHOSH
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Correspondence to PRASENJIT GHOSH.

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Supplementary Information

CCDC-983594 (for 1b), CCDC-978994 (for 2b) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data center via www.ccdc.cam.ac.uk/data_request/cif.

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GANGWAR, M.K., KALITA, A.C. & GHOSH, P. Palladium complexes of a new type of N-heterocyclic carbene ligand derived from a tricyclic triazolooxazine framework. J Chem Sci 126, 1557–1563 (2014). https://doi.org/10.1007/s12039-014-0705-x

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  • DOI: https://doi.org/10.1007/s12039-014-0705-x

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