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On July 16, the reporter learned from the University of Science and Technology of China that Professor Fu Yao, Associate Professor Lu Xi and others from the University of Science and Technology of China have made new progress in the field of alkyl coupling: the research team has developed a cobalt-catalyzed aromatic substructure-assisted olefin hydroalkylation reaction, which has opened up a new way for the synthesis of chiral functional molecules such as deuterated drugs. The relevant research results were recently published online in Nature Synthesis.

Alkyl carbon centers play a role in supporting the "three-dimensional" structure in organic molecules and functional materials, and give these molecules unique properties and functions. Olefin hydroalkylation uses stable and common olefins as raw materials, and reacts metal hydrogen species with olefins to generate alkyl metal intermediates, thereby precisely constructing alkyl carbon centers. However, controlling the stereochemical selectivity of this reaction has always been a challenge, and usually requires the assistance of specific Lewis basic groups or polar heteroatom functional groups.

In response to the above challenges, the team of Fu Yao and Lu Xi conducted in-depth research on the structure and reaction regularity of alkyl metal intermediates, and successfully established a new model that uses CH...π non-covalent interactions (a weak chemical interaction) to control reaction selectivity. In this process, the π electron system of the styrene substrate forms a CH...π interaction with the hydrogen atoms in the catalyst, thereby precisely controlling the stereochemical selectivity of the reaction. This enables the cobalt-catalyzed olefin hydroalkylation reaction to proceed smoothly, accurately constructs the ortho-chiral alkyl carbon center of the aromatic group, and solves the problem of uncontrollable stereochemistry in the hydroalkylation reaction of heteroatom-free olefins. The reaction is applicable to a variety of substrates and has excellent functional group compatibility. In addition, the catalytic system can also achieve deuterated alkylation of olefins, showing application potential in the synthesis and modification of drug molecules and natural products.

The researchers said that this study provides a new model for stereoselective control of olefin functionalization reactions and opens up a new path for the synthesis of chiral functional molecules such as deuterated drugs. (Reporter Wang Qiao, intern Liu Yuning)