Study On The Synthesis Of CF₃-containing Indenes, Phenanthridines And Benzofurans

Indene, phenanthridine and benzofuran derivatives are importantorganic compounds, which are widely existed in biologically activemolecules and natural products. Particularly, phenanthridine derivativeshave been widely used in the field of optoelectronic materials. Inconsideration the importance and the practicability of indene,phenanthridine and benzofuran derivatives, this paper focuses on thedevelopment of new methods for the synthesis of these compounds.The dissertation includes four parts:(1) The recent research on indene, phenanthridine and benzofuranderivatives has been reviewed.(2)A palladium catalyzed tandem carbocyclization-Suzuki couplingreaction of ortho-(2-chlorovinyl)-alkynylbenzenes with boronic acids:synthesis of2-trifluoromethylindenes. Boronic acids are both low costand low toxicity. The reaction was studied for a short time and thepost-processing was convenient.(3) A palladium-catalyzed tandem Suzuki/C H arylation reactions ofN-(2-bromophenyl)-trifluoroacetimidoyl chlorides with boronic acids:synthesis of6(trifluoromethyl)phenanthridines.(4) A two-step, one-pot tandem iodocyclization andtrifluoromethylation have been developed. A variety of3-trifluoromethylbenzofurans were prepared in moderate to good yieldsvia the tandem reaction of2-alkynylanisoles with elemental iodine and(trifluoromethyl)trimethylsilane.