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DOI10.1021/acs.joc.1c01479
Cerium Ammonium Nitrate-Mediated Access to Biaryl Lactones: Substrate Scopes and Mechanism Studies
Chao, Mianran; Wang, Fang; Xu, Linlin; Ju, Yanping; Chen, Zixuan; Wang, Bin; Gong, Peiwei; You, Jinmao; Jin, Ming; Shen, Duyi
通讯作者Chao, MAR ; Shen, DY (通讯作者),Qufu Normal Univ, Sch Chem & Chem Engn, Key Lab Life Organ Anal Shandong Prov, Qufu 273165, Shandong, Peoples R China.
发表日期2021
ISSN0022-3263
EISSN1520-6904
起始页码13371
结束页码13380
卷号86期号:19
英文摘要Herein we described an access to biaryl lactones from ortho-aryl benzoic acids via intramolecular O-H/C-H oxidative coupling with the commonly used cerium ammonium nitrate (CAN) as the one-electron oxidant under a thermal condition. The radical interrupting experiment suggested a radical process, while the kinetic isotope effect (KIE) showed that the C-H cleavage likely was not involved in the rate-determining step. Competitive reactions, especially the strikingly different rho values of Hammett equations, indicated that the reaction rate was more sensitive to the electronic properties on the aryl moiety rather than the carboxylic moiety, which corresponded to the first single electron transfer (SET) step. In addition, the quite negative rho values (-4.7) of the aryl moiety unveiled the remarkable electrophilic nature of the second intramolecular radical addition process, which was also consistent with product yields and regioselectivity. Moreover, control experiments disclosed that the single electron in the third step was also transferred to Ce-IV instead of molecular oxygen. Besides, the possible role of co-solvents trifluoroethanol (TFE) and its influences on the Ce-IV species were discussed. This work elucidated the possible mechanism by proposing the step that had more effects on the total reaction rate and the species that was responsible for the last single electron transfer.
关键词C-H LACTONIZATIONO BOND FORMATIONRADICAL-ADDITIONDEHYDROGENATIVE LACTONIZATIONCATALYZED C(SP(2))-HCARBOXYLIC-ACIDSRATE CONSTANTSOXIDATIONBEHAVIORPOLAR
语种英语
WOS研究方向Chemistry
WOS类目Chemistry, Organic
WOS记录号WOS:000704707200015
来源期刊JOURNAL OF ORGANIC CHEMISTRY (IF:4.745[JCR-2018],4.224[5-Year])
来源机构中国科学院西北生态环境资源研究院
文献类型期刊论文
条目标识符http://gcip.llas.ac.cn/handle/2XKMVOVA/254612
作者单位[Chao, Mianran; Wang, Fang; Xu, Linlin; Ju, Yanping; Chen, Zixuan; Gong, Peiwei; You, Jinmao; Jin, Ming; Shen, Duyi] Qufu Normal Univ, Sch Chem & Chem Engn, Key Lab Life Organ Anal Shandong Prov, Qufu 273165, Shandong, Peoples R China; [Wang, Bin] Univ Jinan, Sch Chem & Chem Engn, Jinan 250022, Peoples R China; [You, Jinmao] Chinese Acad Sci, Northwest Inst Plateau Biol, Xining 810001, Peoples R China
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Chao, Mianran,Wang, Fang,Xu, Linlin,et al. Cerium Ammonium Nitrate-Mediated Access to Biaryl Lactones: Substrate Scopes and Mechanism Studies[J]. 中国科学院西北生态环境资源研究院,2021,86(19).
APA Chao, Mianran.,Wang, Fang.,Xu, Linlin.,Ju, Yanping.,Chen, Zixuan.,...&Shen, Duyi.(2021).Cerium Ammonium Nitrate-Mediated Access to Biaryl Lactones: Substrate Scopes and Mechanism Studies.JOURNAL OF ORGANIC CHEMISTRY,86(19).
MLA Chao, Mianran,et al."Cerium Ammonium Nitrate-Mediated Access to Biaryl Lactones: Substrate Scopes and Mechanism Studies".JOURNAL OF ORGANIC CHEMISTRY 86.19(2021).
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