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Photochemical O-H Functionalization of Aryldiazoacetates with Phenols via Proton Transfer.
Organic Letters ( IF 5.2 ) Pub Date : 2020-08-31 , DOI: 10.1021/acs.orglett.0c02564
Claire Empel 1, 2 , Sripati Jana 1 , Chao Pei 1 , Thanh Vinh Nguyen 2 , Rene M Koenigs 1, 2
Affiliation  

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 pKA 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.

中文翻译:

通过质子转移用苯酚对重氮乙酸乙酸酯进行光化学OH功能化。

在这项工作中,我们报告了对酚与芳基重氮乙酸酯反应的彻底研究。使用不同光谱方法进行的机械研究和理论计算表明,苯酚和芳基重氮乙酸酯之间存在氢键,该氢键可通过酚的酸度进行调节。苯酚的p K A以及因此的氢键在随后的光致质子转移反应中起重要作用,从而得到苯酚的正规O–H官能化产物。
更新日期:2020-09-20
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