Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University, Shenzhen Graduate School, Shenzhen, 518055, China.
Shenzhen SynLED Technology Limited, 2-104, BIO-Incubator, Gaoxin C, 1st Ave., Shenzhen Hi-Tech Industrial Park, Nanshan, Shenzhen, 518057, China.
Angew Chem Int Ed Engl. 2018 Feb 19;57(8):2174-2178. doi: 10.1002/anie.201712384. Epub 2018 Jan 24.
Aldehydes are among the most versatile functional groups for synthetic chemistry. However, access to polysubstituted alkyl aldehydes is very limited and requires lengthy synthetic routes that involve multiple-step functional-group conversion. This paper reports a one-step synthesis of polysubstituted aldehydes from readily available olefin substrates using visible-light photoredox catalysis. Despite a number of competing reaction pathways, commercial styrenes react with vinyl ethers selectively in the presence of an acridinium salt photooxidant and a disulfide hydrogen-atom-transfer catalyst under blue LED irradiation. Alkyl aldehydes with different substitution patterns are prepared in good yields. This strategy can be applied to structurally sophisticated substrates.
醛基是合成化学中用途最广泛的官能团之一。然而，多取代的烷基醛的获得非常有限，需要通过多步官能团转化的冗长合成路线来实现。本文报道了一种使用可见光光氧化还原催化，从易得的烯烃底物一步合成多取代醛的方法。尽管存在许多竞争反应途径，但在吖啶盐光氧化剂和二硫氢转移催化剂的存在下，商业苯乙烯在蓝 LED 照射下与乙烯基醚选择性反应。不同取代模式的烷基醛以良好的产率制备。该策略可应用于结构复杂的底物。
