The C-C Cross-coupling Reactions Of1,2-di(pyrimidin-2-yl) Disulfide With Arylboronic Acids/Alkynes

Disulfides play a vital role in living systems with respect to the folding, stabilityand activity of numerous proteins. They are also of great interest as cleavable linkagesfor the design of drug delivery systems. In organic chemistry, disulfides are used asintermediates for the synthesis of sulfinyl and sulfenyl compounds. In industry, theyare of great importance as vulcanizing agents. In addition, it is known that differentheterocyclic disulfides have interesting cytotoxic activity. Disulfide-containing arylgroup is widely used in functional materials, synthetic chemistry and medicine. Dueto the instability of disulfide bond, it is replaced and restored by reducing agent whendisulfides decomposed to the corresponding thioalcohol nucleophile's attackingbreaks the disulfide bonds, the formation of two new thiol or thioether. In recent years,scientists have carried out the synthesis of disulfides and sulfide-related reactions intofurther research, having greatly expanded from raw materials to the catalyst. This typeof redox reactions has a very important useage on living body and medicine.This paper summarizes the1,2-di(pyrimidin-2-yl)disulfide and its ramificationand arylboronic acids have C-C cross-coupling reactions, and the progress of havingC-C cross-coupling reaction with alkynes.This is the first time based on the C-S toget the C-C cross-coupling products, so that a reaction of this type has been furtherdeveloped.The main research results are as follows:1?Firstly,1,2-di(pyrimidin-2-yl)disulfides were prepared via the oxidation of3,4-dihydro-2-thione derivatives in the presence of2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and NaH. Then, an efficient method forcarbon-carbon bond formation is described. The process employs palladium-catalyzedcopper-mediated in1,4-dioxane cross-coupling of dipyrimidin disulfides witharylboronic acids deliver C-C coupling products through unreactive C–S bondcleavage.2?Under the similarly conditions, the reaction of dipyrimidin disulfides withalkynes was also carried out leading to the C-C coupling products. A possiblemechanism was also proposed. 3?The Suzuki–Miyaura and Sonogashira type cross-coupling reactions ofdiheteroaryl disulfides with arylboronic acids and alkynes to give the C-C couplingproducts were also studied.