China Keda olefin hydrogenation reaction research progress

June 19, 2020

China Keda olefin hydrogenation reaction research progress

Recently, Professor Fu Jiong of the University of Science and Technology of China, in collaboration with Professor Liu Lei of Tsinghua University, has made new progress in the hydrogenation reaction of olefins and their applications. The research was published on Nature Communications, April 2 (DOI: 10.1038/ncomms11129). The first author of the dissertation was Dr. Lu Wei and associate professor Xiao Bin from the University of Science and Technology of China.

Olefins are an important molecule in organic chemistry and are the main raw materials for petrochemicals. Alkenyl functional groups are also common in a variety of complex natural products and drug molecules, such as cinchona, vitamin D2 and so on. Metal-catalyzed olefin conversion reactions include classic name reactions such as the Heck reaction. In recent years, significant progress has been made in the study of the bond-saturation of saturated carbon-carbon bonds, which breaks through the limitations of the traditional inverse synthesis analysis that relies on the cleavage of adjacent sites in functional groups. However, such reactions often require the use of metal reagents, the structure of the substrate is also limited, and they are sensitive to air and water. Replacing conventional organometallic reagents with inexpensive, easily available, relatively stable olefins to achieve saturated carbon-carbon bond formation reactions is not only a novel concept but also a practical method.

Fu Hao's group developed a nickel-catalyzed olefin reductive coupling reaction. With the participation of silanes, olefins played the roles of alkyl metal reagent equivalents and participated in the formation of saturated carbon-carbon bonds. The reaction uses olefin as a direct reaction raw material, overcomes the problem of source and storage of metal reagents, and the reaction has excellent functional group compatibility and can be used for the modification of complex natural products. Vitamin D2 contains alkenyl functional groups in various chemical environments. Through this hydrogenation reaction of olefins, alkyl modification can be performed with high chemical selectivity at terminal olefin sites. The cinchonidine-type molecule has a wide range of applications in the field of asymmetric phase transfer catalysis, and through the alkylation modification of the cinchonidine intramolecular double bond, more potential novel phase transfer catalysts have been obtained. In addition, the effect of this reaction on the simplest conversion of ethylene gas was also investigated. With ethylene gas, hydrogenation was smoothly achieved at atmospheric pressure, making ethylene gas a simple and effective carbon-based source.

This work demonstrated the hydrogenation of olefins and its application in complex molecular modification. The proposed concept of replacing conventional organometallic reagents with olefins opens up new ideas for metal-catalyzed cross-coupling reactions, directly for olefins. Utilization provides a new way.

The above research was supported by the National Basic Research Development Program ("973" Program) and the National Natural Science Foundation of China.

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