Application Of C-h Activation/C-h Functionalization In Cascade Reactions And The Construction Of C-C, C-N And C-O Bond

Recently, C-H activation/C-H functionalization has been the research topic for the demand from Green Chemistry and the development of organic synthesis. Using this method to construct new chemical bond, which start directly from C-H bond, without any pre-functionalization, has been extensively employed in the synthesis of complicated molecules and nature products. Particularly, our attention was focused on the use of C-H activation/C-H functionalization to construct new chemical bond and complicated compounds in cascade reactions.This dissertation, consisted of four chapters, was about the use of C-H activation/C-H functionalization to construct new C-C, C-X bonds and the synthesis of new complicated compounds in one-pot cascade reactions. Based on the designation of reactant and the development of catalytic system, onset of fused-ring compounds with complicated structure were synthesized effectively.Firstly, we abstracted the research development of the C-H activation in recent years. Made our best to collect the diversity ways to make the activation of C-H bond to come true, and collected the use of C-H activation in cascade reaction as possible as we can.Secondly, using Cu(OAc)2/O2as the reaction catalyst, we synthesized1,2-disubstituded benzimidazoles and quinazolines directly from diarylcarbodiimides or benzylphenylcarbodiimides. This reaction combined the nucleophilic addition and intramolecular C-H activation in a one-pot cascade reaction.Thirdly, under the co-catalyze of Cul and Pd(dppf)Cl2, nucleophilic addition and Ullmann coupling were combined with intramolecular C-H activation in one pot. Series of6H-isoindolo[2,1-a]indol-6-ones were synthesized from commonly used benzoyl chloride and o-gem-dibromovinyl aniline, which would be very applicable in the synthesis of indole and its derivates.Lastly, the use of C-H activation/C-H functionalization to construct C-O bond was conducted. Using DDQ as the oxidant, without any metal catalyst, we constructed C-O bond via a cross dehydrogenative coupling between isochroman and oxime.