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Keywords:

  • C–H Activation;
  • Palladium;
  • Chelates;
  • Metalation;
  • Benzamidinates

Abstract

The pendant benzamidines {Ph–C[=N–(2,6-di-iPr-C6H3)](NHE)} [E = (CH2)2NMe2, CH2Py] and their palladium complexes [(Ph–C{=NE}{NH–(2,6-di-iPr-C6H3)})Pd(OAc)2] [E = (CH2)2NMe2 (1), CH2Py (2)] have been prepared. Upon heating, the corresponding palladacyclic complexes, [({η1-C6H4}–C(=NE){NH–(2,6-di-iPr-C6H3)})PdOAc] [E = (CH2)2NMe2 (3), CH2Py (4)], were obtained. Due to the substituent groups on the ortho positions of the phenyl ring attached to the nitrogen atom of the amidinate group, the C–H bond activation process was observed on the ortho position of the phenyl ring attached to the carbon atom of the amidinate group. This process can be proved by X-ray structural determination. The molecular structures are reported for compounds 1 and 4. Catalytic application of cyclopalladated derivatives 3 and 4 toward the Suzuki reaction was also investigated.