| Aromatic compounds processing C–X bonds(e.g.,C-S,O,N etc.)are widely distributed in the nature,and they are widely used in multiple areas,including pesticides,pharmaceutical industry,material science and so on.Therefore,C–X coupling strategies are a momentous research project in modern organic synthesis.Transition metals catalyzed cross-coupling reactions of aryl halides with nucleophiles containing heteroatoms to complete C-X bonds formation are the main techniques of traditional synthesis.Above mentioned method has certain limits and disadvantages,such as the use of expensive metal catalysts,strong base and complicated ligands.In view of green chemistry,we have designed several carbon-heteroatom bond formation reactions by using iodide or copper salts as an accelerant or catalyst.The content contains the following four parts in this thesis.A novel and convenient approach for the preparation of β-alkoxy sulfides by using NaI as a promoter to achieve three-component oxysulfenylation reaction of alkenes with arylsulfinic acids as a sulfur sources and alcohols as a nucleophiles in the presence of HBr as an additive.Green,highly efficient and mild conditions and wide application are the advantages of the present method.In addition,2-substituted-2,3-dihydrobenzofuran was obtained through intra-molecular condensation reaction by using 2-allylphenol as a subtrate.In the third chapter,β?acetamido sulfides and β?acetoxy sulfides were obtained by two different synthetic methods,respectively.The synthesis of β?acetamido sulfides via difunctionalization of alkenes with thiophenols and nitriles as substrates in the presence of N-Bromosuccinimide as an additives.On the other hand,the synthesis of β?acetamido sulfides via iodine catalyzed 1,2-acetoxysulfenylation of alkenes with thiophenols and(Diacetoxyiodo)benzene as substrates in the presence of dimethyl sulfoxide as an oxidizing agent.Meanwhile,β?acetamido sulfides were also synthesized when we use 1-(arylthio)pyrrolidine-2,5-dione instead of thiophenols in the presence of HBr in moderate yield.In chapter four,we choose arylsulfonyl chlorides as thiolation reactants under TBAI-HBr system promoted direct sulfenylation of various rich electronic compounds(such as phenols,pyrazolones,indoles and related heteroarenes)in good to excellent yields.The characteristic of the present protocol is green,efficient and mild conditions,low cost and wide application.In the final chapter,we studied CuBr promoted Oxidative Functionalization of C(sp3)-H Bonds(Ethers,Toluenes and olefins containing C(sp3)-H Bonds at the α position)with Isoquinolines to get N-alkyl(benzyl)isoquinolin-1(2H)-ones.Furthermore,this procedure provides a simple method to afford 5-oxaprotoberberinones and their derivatives. |
