Preparation of benzoyl fluorides and benzoic acids from phenols via a dearomatization-rearomatization strategy

作者全名："Yang, Meixian; Huang, Xinyue; Miao, Wenjun; Yi, Lan; Cai, Jiajing; Zhao, Zhenghuan; He, Jia; Qiu, Dachuan"

作者地址："[Yang, Meixian; Miao, Wenjun; Yi, Lan; Cai, Jiajing; Zhao, Zhenghuan; Qiu, Dachuan] Chongqing Med Univ, Sch Basic Med Sci, Dept Radiat Med, Chongqing 400016, Peoples R China; [He, Jia] Chongqing Med Univ, Inst Life Sci, Ctr Novel Target & Therapeut Intervent, Chongqing 400016, Peoples R China; [Huang, Xinyue] Chongqing Univ Technol, Coll Chem & Chem Engn, Chongqing 400054, Peoples R China"

通信作者："Qiu, DC (通讯作者)，Chongqing Med Univ, Sch Basic Med Sci, Dept Radiat Med, Chongqing 400016, Peoples R China.; He, J (通讯作者)，Chongqing Med Univ, Inst Life Sci, Ctr Novel Target & Therapeut Intervent, Chongqing 400016, Peoples R China."

来源：ORGANIC CHEMISTRY FRONTIERS

ESI学科分类：CHEMISTRY

WOS号：WOS:000947758800001

JCR分区：Q1

影响因子：5.4

年份：2023

卷号：10

期号：8

开始页：1975

结束页：1980

文献类型：Article

关键词：　

摘要："We describe here a method to generate both benzoyl fluorides and benzoic acids using 2,5-cyclohexadienones prepared from phenols via oxidative dearomatization. 2,5-Cyclohexadienones react with difluoromethyl 2-pyridyl sulfone under basic conditions to give gem-difluoroolefins in situ, which could be attacked by nucleophiles and further aromatized to form benzoyl fluorides. By changing the reaction conditions, benzoic acids could be formed efficiently in a one-pot fashion as well. The mild conditions and broad substrate scope make this transformation a unique approach for formal deoxyacylation of phenols without transition metal catalysis."

基金机构："NSFC [82001869, 51904053]; Creative Research Group of CQ University [CXQT21017]; Science and Technology Research Program of Chongqing Municipal Education Commission [KJQN202200446, KJQN202101142]"

基金资助正文："The authors gratefully acknowledge the research support of this work by NSFC (82001869 and 51904053), Creative Research Group of CQ University (CXQT21017), and the Science and Technology Research Program of Chongqing Municipal Education Commission (Grant No. KJQN202200446, KJQN202101142)."