Study On Metal-free Intermolecular Aminofluorination Of Conjugated Dienes

Containing nitrogen or fluorine molecules are widely applied in pharmaceuticals and agricultural chemicals, due to their good medical and biological activity. Hence, introducing the containing nitrogen or fluorine functional group into molecular is significance and has potential practical application.Recently, the introducing two different functional groups into unsaturated carbon-carbon bond simultaneously(difunctionalization of unsaturated carbon-carbon bond), which has highly step-economical and has been attracted much attention. Owing to the extremely importance of fluorinated molecules, a series of difunctionalization of unsaturated hydrocarbons have been successfully developed, such as: oxyfluornlation, hydrofluorination,carbofluorination phosphonofluorinaton and fluorosulfonylation, etc. Additionally,amino/functionalization of unsaturated hydrocarbons, such as: diamination,aminooxygenation, aminobortion and aminohalogenation have also been disclosed, science the containing nitrogen compounds are ubiquitous structural motifs in bioactive molecules.Compared with the amino/functionalization or fluoro/functionalization, the aminofluorinatin of unsaturated hydrocarbons has attracted less attention, moreover, the expensive and toxic transition-metals are necessary in most of these transformations.In this thesis, employing commercially available N-fluorobenezenesulfonamide(NFSI)both as fluorine and nitrogen sources, reacted with the eaily prepared 1-aryl-1,3-dienes affording the aminofluorination of alkenes with highly regioselectivtiy have been realized under metal-free conditions. This method provides a new avenue to the synthesis of the vicinal amino and fluorine molecules. Finally, we discuss the proposed the mechanism of this reaction.