The Studies On Free-Radical-Promoted Selective Addition Of C(sp~3)-H To Alkenes

Research and interest in C-H functionalization reactions have continuously grown during the past several years.The research offer effective appoaches toward connecting molecular fragments that are often complementary to traditional methods.Thanks to the development of transition-metal catalysis and free radical methods,great achievement in the area has been made.In this paper,we first summarized the latest advances in this field.Then our several investigations on free-radical-initiated selectively activation of C-H bond to form C-C were introduced in details.Finally we summed up the developments and the future in this area.This thesis mainly contains the following five sections.In the first chapter,we summarized the developments of activation of C-H bond to form C-C,and this chapter can be devided into two parts,?1?transition-metal-catalyzedC–Halkylation;?2?free-radical-initiatedC–H functionalization.In the second chapter,we demonstrated an H-bonding-induced radical addition of simple alcohols to unactivated olefins,which allowed a convinent and effective access to diverse primary,secondary and tertiary alcohols,diols,and even polyfluorinated alcohols.In the third chapter,we developed a KI-mediated radical anti-Markovnikov addition of simple ketones and esters to unactivated alkenes.Through this strategy,a wide range of complex carbonyl compounds can be conveniently synthesized in high selectivities.In the fourth chapter,we depicted a Cu?II?-promoted free radical addition of alkanes to unactivated alkenes.a diverse range of functionalization alkanes was achieved via selective activation of the C?sp³?-H bonds.In the five chapter,metal-free radical cascade dichloromethylation of activated alkenes using CH₂Cl₂ was developed,which allows efficient access to dichloromethylated oxindoles by selectively functionalization of the C-H bond of DCM.Finally,we summarized our research on free-radical-initiated C-H functionalization,and the future work was also discussed.