Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, China.
Nat Commun. 2021 Aug 12;12(1):4904. doi: 10.1038/s41467-021-25222-1.
Alkynes are amongst the most valuable functional groups in organic chemistry and widely used in chemical biology, pharmacy, and materials science. However, the preparation of alkyl-substituted alkynes still remains elusive. Here, we show a nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts. Key to the success of this coupling is the development of an easily accessible and bench-stable amide-type pincer ligand. This ligand allows naturally abundant alkyl amines as alkylating agents in Sonogashira reactions, and produces diverse alkynes in excellent yields under mild conditions. Salient merits of this chemistry include broad substrate scope and functional group tolerance, gram-scale synthesis, one-pot transformation, versatile late-stage derivatizations as well as the use of inexpensive pre-catalyst and readily available substrates. The high efficiency and strong practicability bode well for the widespread applications of this strategy in constructing functional molecules, materials, and fine chemicals.
炔烃是有机化学中最有价值的官能团之一，广泛应用于化学生物学、药学和材料科学。然而，烷基取代的炔烃的制备仍然难以捉摸。在这里，我们展示了一种镍催化的去氨基 Sonogashira 偶联反应，用于烷基吡啶盐。该偶联反应成功的关键在于开发了一种易于获得且稳定的酰胺型钳形配体。这种配体允许天然丰富的烷基胺作为 Sonogashira 反应中的烷基化试剂，并在温和条件下以优异的收率得到多种炔烃。该化学的显著优点包括广泛的底物范围和官能团耐受性、克级合成、一锅转化、多功能的后期衍生化以及使用廉价的预催化剂和易得的底物。这种策略的高效率和强实用性为其在构建功能分子、材料和精细化学品方面的广泛应用奠定了基础。
