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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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Title Palladium complexes of a new type of N-heterocyclic carbene ligand derived from a tricyclic triazolooxazine framework
 
Creator GANGWAR, MK
KALITA, AC
GHOSH, P
 
Subject Palladium
tricyclic triazolooxazine derived N-heterocyclic carbene (NHC)
PEPPSI
RING-OPENING POLYMERIZATION
MIXED AQUEOUS-MEDIUM
INTRAMOLECULAR INTERACTIONS
STEREODIRECTING LIGANDS
ASYMMETRIC CATALYSIS
GOLD(I) COMPLEXES
NHC LIGANDS
SILVER
AIR
CYCLOADDITION
 
Description 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.
 
Publisher INDIAN ACAD SCIENCES
 
Date 2014-12-28T08:58:28Z
2014-12-28T08:58:28Z
2014
 
Type Article
 
Identifier JOURNAL OF CHEMICAL SCIENCES, 126(5)1557-1563
0974-3626
0973-7103
http://dx.doi.org/10.1007/s12039-014-0705-x
http://dspace.library.iitb.ac.in/jspui/handle/100/16240
 
Language English