Manoharan Karthikeyan, Bieszczad Bartosz
Centre for Synthesis and Chemical Biology, School of Chemistry, University College Dublin, Belfield, D04 V1W8 Dublin, Ireland.
School of Chemical and Pharmaceutical Sciences, Technological University Dublin, City Campus, Grangegorman, D07 H6K8 Dublin, Ireland.
Molecules. 2024 Aug 13;29(16):3844. doi: 10.3390/molecules29163844.
Acyl-1,4-dihydropyridines have recently emerged as universal acylation reagents. These easy-to-make and bench-stable NADH biomimetics play the dual role of single-electron reductants and sources of acyl radicals. This review article discusses applications of acyl-1,4-dihydropyridines in organic synthesis since their introduction in 2019. Acyl-1,4-dihydropyridines, activated by photochemical, thermal or electrochemical methods, have been successfully applied as radical sources in multiple diverse organic transformations such as acyl radical addition to olefins, alkynes, imines and other acceptors, as well as in the late-stage functionalisation of natural products and APIs. Release of acyl radicals and an electron can be performed under mild conditions-in green solvents, under air and sunlight, and without the use of photocatalysts, photosensitizers or external oxidants-which makes them ideal reagents for organic chemists.
酰基-1,4-二氢吡啶最近已成为通用的酰化试剂。这些易于制备且在实验室条件下稳定的NADH模拟物发挥着单电子还原剂和酰基自由基来源的双重作用。这篇综述文章讨论了自2019年引入以来酰基-1,4-二氢吡啶在有机合成中的应用。通过光化学、热或电化学方法活化的酰基-1,4-二氢吡啶已成功用作多种不同有机转化中的自由基来源，例如酰基自由基加成到烯烃、炔烃、亚胺和其他受体上，以及在天然产物和活性药物成分的后期官能化中。酰基自由基和一个电子的释放可以在温和条件下进行——在绿色溶剂中、在空气和阳光下，并且无需使用光催化剂、光敏剂或外部氧化剂——这使其成为有机化学家的理想试剂。
