New Methods For The Formationon Of C-N Bonds Involving Aryl Halides

In this thesis, two new methods for the formation of C-N bonds involving aryl halides were developed, including a novel N-heterocyclic carbene-palladium complex catalyzed C-N coupling reaction of aryl chlorides with primary and secondary amines, and transition metal-free, base-promoted C-N coupling reaction between aryl halides and tertiary amines:1) A type of novel and well-defined N-heterocyclic carbenepalladium(II)-2-aryl-4,5-dihydrooxazole complexes was developed and they are efficient catalysts in the C-N coupling reaction of aryl chlorides with primary and secondary amines. Under the optimal conditions, all reactions took place smoothly to give the desired products in high yields.2) The first example of C-N coupling reaction between tertiary amines and aryl halides were developed. Under the transition metal-free, basepromoted conditions, tertiary amines can react with aryl halides to form new C-N bond via aryne intermediates. Therefore, a new method for the formation of C-N bonds was developed under green and mild conditions to give mono-arylated tertiary amines in high selectivity.