Nickel-catalyzed Direct Formation Of C-s Bond Of Aryl Sulfides From Arysulfonyl Chlorides And Aryl Iodides

Organosulfur compounds are indispensable chemical substances to life,and widely exist in many Biological macromolecules,materials science,pharmaceutical,agricultural and chemical agents.Arylsulfonyl chlorides are inexpensive,safe and readily available compounds.They have been widely used as the protecting groups and sulfonylating agents in materials science and medicinal chemistry over a century.The utilization of arylsulfonyl chlorides concerning the C-S bond coupling reaction generally produced the congenerical species of aryl sulfones,or disulfides to the end.The transition-metal-catalyzed direct formation of aryl sulfides from arylsulfonyl chlorides was rarely reported.So far,the synthesis of aryl sulfides through direct construction of arylsulfonyl chlorides with aryl halides has not been found.There is yet an attractive and topical project of the C-S cross-coupling reaction by sulfhydrylation of arylsulfonyl chlorides.The thesis includes two chaptersThe progress of C-S coupling reaction by transition-metal-catalyzedIn this Chapter,a brief introduction of the C-S coupling reaction in sulfide and benzothiazole derivatives synthesis was given.Different metal compounds such as Pd,Ni,Cu,Co,Fe and In catalyzed C-S coupling reactions and different sulfur sourcees as substrates were described.Nickel-catalyzed direct formation of C-S bond of aryl sulfides from arylsulfonyl chlorides and aryl iodidesVarious unsymmetrical aryl sulfides were synthesized by nickel-catalyzed C-S bond formation in good to excellent yields.The reactions employed arylsulfonyl chlorides as aryl thiol source and Mn dust as reducing agent.Mechanistic studies revealed the existence of intermediate disulfide substance.A catalytic cycle was proposed including a three-step reduction by Mn for the achievement of reaction,and Ni(0)and Ni(I)species were supposed to be involved in the reaction mechanism.