Liu Lei, Xu Zhenhui, Liu Tao, Xu Chao, Zhang Wangqin, Hua Xiangqi, Ling Fei, Zhong Weihui
College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, Zhejiang 310014, People's Republic of China.
College of Pharmacy, Qiqihar Medical University, Qiqihar, Heilongjiang 161006, People's Republic of China.
J Org Chem. 2022 Sep 2;87(17):11379-11386. doi: 10.1021/acs.joc.2c00856. Epub 2022 Aug 11.
Herein, an atom-economical and eco-friendly electrochemical oxidation/cyclization of glycine derivatives through intramolecular Shono-type oxidative coupling is disclosed, leading to a variety of 2-substituted benzoxazoles in 51-85% yields. This oxidative cyclization proceeded in transition metal- and oxidant-free conditions and generated H as only a byproduct. Additionally, gram-scale reactions and a broad substrate scope demonstrated the synthetic usefulness of this protocol.
在此，我们报道了一种通过分子内Shono型氧化偶联实现的甘氨酸衍生物的原子经济且环境友好的电化学氧化/环化反应，该反应可生成多种2-取代苯并恶唑，产率为51-85%。这种氧化环化反应在无过渡金属和无氧化剂的条件下进行，仅产生氢气作为副产物。此外，克级规模的反应和广泛的底物范围证明了该方法的合成实用性。
