Empel Claire, Jana Sripati, Pei Chao, Nguyen Thanh Vinh, Koenigs Rene M
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany.
School of Chemistry, University of New South Waley, Sydney 2052, Australia.
Org Lett. 2020 Sep 18;22(18):7225-7229. doi: 10.1021/acs.orglett.0c02564. Epub 2020 Aug 31.
In this work, we report a thorough investigation of the reaction of phenols with aryldiazoacetates. Mechanistic studies using different spectroscopic methods and theoretical calculations suggest a hydrogen bond between phenol and aryldiazoacetates, which can be modulated by the phenol acidity. The p of phenol and therefore the hydrogen bond plays an important role in a subsequent photoinduced proton transfer reaction to give the formal O-H functionalization product of phenols.
在本研究中，我们报告了对酚类与芳基重氮乙酸酯反应的全面研究。使用不同光谱方法和理论计算进行的机理研究表明，酚类与芳基重氮乙酸酯之间存在氢键，该氢键可由酚的酸度调节。酚的pKa以及因此氢键在随后的光诱导质子转移反应中起着重要作用，以生成酚类的形式上的O-H官能化产物。
