Studies On The Formation Of C-C/C-S Bonds Via Palladium- And Copper-catalyzed Coupling Reactions Of Sulfamides/ Sulfinates

This thesis gives an overview of the reactions of organosulfur compounds used as the acyl sources and/or sulfonyl sources firstly. Secondly, the palladium/cupper-catalyzed acylation of benzoxazoles by using sulfamines as the acylation reagents were developed in the first time. Finally, a protocol for the facile synthesis of disarylsulfones via copper-catalyzed arylboronic acid using arenesulfinic acid salts as the sulfonyl sources was established.The acylation of benzoxazole with sulfamines as the acyl source was performed in the presence of Cu Br2 as the oxidant, Na2CO3 as the additive employing palladium trifluoroacetate as the catalyst, respectively, affording the acylated products in mostly moderate condition(Scheme 1). This transformation can tolerate electron-withdrawing group well. All the new compounds were characterized by 1H NMR, 13 C NMR.A new route to disarylsulfones via copper(Ⅱ) complex-catalyzed C-S coupling reaction of arylboronic acid with arenesulfinic acid salts was developed. Note that this reaction utilized arylmethyl arenesulfinic acid salts as a cheap sulfonyl sources and copper(Ⅱ)-1,10 phenanthroline complex as a easily available catalyst, affording the desired products in mostly moderate to good yields(Scheme 2). This transformation can tolerate various functional groups well, and provide a convenient way for the synthesis of disarylsulfones. All the new compounds were characterized by 1H NMR, 13 C NMR.