Lron(Ⅲ)-catalyzed Aerobic Oxidation And Cleavage/Formation Of C-S Bond

In the past few decades, the reactions using transition metal-catalysts have turned into an indispensable branch in organic synthesis. The factors, such as cheap, readily abundant, environmentally friendly and many others give iron catalyst advantages over other expensive transition metal catalysts. As a result, iron catalysis has proved to be a novel hotspot in the research of transition metal catalysis. However, the iron-catalysts’ development has some limitations, for instance, the smaller range of iron-catalyzed reaction and the lower ability of iron catalyst. Therefore, the development of high efficiency iron-catalyzed synthesis has remarkable practical and theoretical value.β-keto sulfone compound is a kind of indispensable sulfur-containing compounds. It acts not only as an intermediate in the Michael addition reaction, but also as a precursor in the synthesis of allenes, acetylene, ketone, vinyl sulfones and polymeric of4H-pyran addition. In addition, β-keto sulfone plays an important role in the formation of β-hydroxy-α-halomethyl sulfone and sulfoxide which have optically activity.In this paper, we demonstrated an efficient method for the synthesis of β-keto sulfone compounds by iron catalysis from various substituted styrene and dimethyl sulfoxide with hydrazine hydrate, using O2as oxidant. Then we examined the optimum conditions and investigated the compatibility of styrene with various functional groups. Additionally, we proposed a plausible reaction mechanism that is based on isotope tracing experiments, efficient and extensive applicability of functional groups gave the synthesis a decided advantage. Wherein, the procedure of carbon-sulfur bond cleavage/formation is a key step in this synthetic method. For the reason that β-keto sulfones are commonly used intermediates in reactions, our research has found an increasingly wide application of total synthesis.