Metal Catalyst-Free Oxidative Cleavage of Aryl C(OH)-C Bonds

作者：Li, Chi; Gao, Yu; Li, Han; Li, Wenhao; Wang, Xinmei; Wang, Xuerong; Lin, Chunguang; Wang, Jinhui^*; Li, Yiying^*; Xu, Huanjun^*

来源：ChemistrySelect, 2023, 8(34): e202301252.

DOI：10.1002/slct.202301252

• Aerobic oxidation
• Alcohol
• Carbonyl compounds
• Metal-free

A simple and efficient protocol for oxidative cleavage of aryl C(OH)-C bonds to acids was reported. In this protocol, KOtBu was found to be able to transform aryl alcohols and ketones to the desired benzoic acids without any other additives using 4 MPa O2 in mesitylene. Substrates with either electron-donating or electron-withdrawing groups could be transformed to the according benzoic acids in moderate to excellent yield. All these findings indicated that this oxidation of aryl secondary C(OH)-C bonds might proceed through a radical mechanism. And the represent lignin dimer model compound was successfully transformed to the benzoic acid, which indicated this protocol might has the potential to transform nature lignin. @@@ KOtBu was found to be able to transform aryl alcohols and ketones to the desired benzoic acids without any other additives using 4 MPa O2 in mesitylene. All aryl C(OH)-C bond in substrates with either electron-donating or electron-withdrawing groups could be transformed to the according benzoic acids in moderate to excellent yields. All findings indicated that the oxidation of aryl secondary C(OH)-C bonds might proceed through a radical mechanism.+image

• 单位
  海南医学院; 哈尔滨医科大学