Visible-light Catalyzed Substitution Reactions Of Indole And Benzene Derivatives

Visible-light-promoted organic reactions become an important area of the organicsynthesis in recent years, as it is environmentally friendly, operationaly simple, andhighly efficient, etc.The chemistry of indole synthesis and functional group transformation has attract-ed and continues to attract interests from synthetic organic chemists because indolemoiety exists in countless biologically active molecules.3-Formylindoles are versatilestarting materials for the synthesis of a broad range of indole derivatives.Although homolytic aromatic substitution has recently been studied intensively,Sulfoxides and sulfones act as aryl radical precursors has never been reported. We havedeveloped a visible-light promoted aryl radical formed from sulfoxides and sulfones,followed by HAS reaction to afford biphenyl derivatives.This dissertation is divided into three parts:The first chapter is a review of visible-light photoredox catalysis in organic systhe-sis.The second chapter introduces an aerobic visible-light photoredox indole C-3formylation reaction. This reaction uses an organic dye Rose Bengal as the photocata-lyst, molecular oxygen as the terminal oxidant, TMEDA as the one-carbon source. In-dole C-3formylation was achieved through C-N bond cleavage.The third chapter is about our research on visible-light-promoted phenyl free radi-cal formed from aryl sulfoxides and sulfones. Biphenyl compounds were synthesizedthrough HAS reaction of phenyl free radical with benzene deravatives and several het-eroaromatic compounds.