Studies On The C-H Bond Functionalization Induced By Radical Cation Salts

The CDC reactions of glycine derivatives were studied, producing a series ofsubstituted quinolines in high yields. Furthermore, A catalytic-sp3C-H oxidation ofpeptides and glycine amides was achieved under radical cation salt catalyzedconditions in the presence of O2, producing a series of substituted quinolines. Finally,we have developed the C-H functionalization reaction between glycine derivativesand1,3-dicarbonyls under catalytic radical cation induced conditions, synthesizing aseries of1,4-dihydropyridine derivatives. The details were showed as follows:(1) A direct construction of quinoline fused lactone and lactam was achieved bycatalytic radical cation salt induced sp3C-H bond oxidation. The polycycle productwas formed in one step from accessible starting materials, avoilding tedious syntheticprocess.(2) A peroxy radical cation intermediate, which was generated by the couplingbetween O2and catalytic TBPA+, can initiate the Csp3-H functionalization of glycineamides derivatives or peptides, producing a series of quinolines.(3) A fragment-reassembly strategy was applied to the construction of biologicallyrelevant1,4-dihydropyridines and phosphorus1,4-dihydropyridines under catalyticradical cation salt induced Csp3H functionalization of glycine derivatives.Mechanistic studies show that domino Csp3-H bond oxidation and C-N bond cleavageare involved.