关键词: 铜氢催化, 不饱和烃, 金属有机试剂, 亲核加成

Abstract: The addition reactions of organometallics such as organolithium reagents, Grignard reagent, organocopper reagents and organoaluminum reagents to aldehydes and ketones are crucial in organic chemistry, and represent one of most classic methods for C―C bond construction. However, such organometallics are limited in their wide applications due to their poor functional group compatibility, sensitivity to water and air and difficulties in storage. As a consequence, the development of new methods with stable, readily available unsaturated hydrocarbons instead of organometallics to participate in various transformations have attracted significant attention. In this article, we primarily focus on the methodology of using unsaturated hydrocarbons converting into catalytic loading of organocopper intermediates under copper-hydride catalysis, instead of traditional stoichiometric amount of organometallics, to implement the addition reactions to aldehydes and ketones. This approach effectively overcomes the limitations associated with traditional methodologies. The introduction of these reactions can enrich and expand the content of nucleophilic addition knowledge in basic teaching processes, broaden students’ perspectives and thinking, facilitate their understanding of the current developments in the field, and stimulate their interest.

Key words: Copper hydride catalysis, Unsaturated hydrocarbons, Organometallics, Nucleophilic addition