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Hexafluoroisopropanol (HFIP)-prompted rearrangement of N-phenoxysulfonamides for the direct assembly of ortho-sulfonamide phenols: A combined experimental and computational study

文献类型：期刊论文

作者Wang, Yi1,2,3; Chen, Xiaoli4; Lin, Shuang1,2,3; Gao, Hui1,2,3; Liu, Fu-Xiaomin1,2,3; Zhou, Zhi1,2,3; Yi, Wei1,2,3
刊名TETRAHEDRON LETTERS
出版日期2022-01-19
卷号89页码:5
关键词N-phenoxysulfonamides Ortho-sulfonamide phenols Rearrangement Hexafluoroisopropanol DFT calculations
ISSN号0040-4039
DOI10.1016/j.tetlet.2021.153601
通讯作者Gao, Hui(gaoh9@gzhmu.edu.cn) ; Zhou, Zhi(zhouzhi@gzhmu.edu.cn) ; Yi, Wei(yiwei@gzhmu.edu.cn)
英文摘要ortho-Sulfonamide phenols represent a class of attractive structural motifs in medicinal and synthetic chemistry. Herein an efficient metal-free rearrangement reaction has been developed for the construction of ortho-sulfonamide phenols via HFIP-prompted intramolecular sulfonamide group 1,3-migration. This protocol features mild reaction conditions, broad functional group compatibility and good regioselectivity. Combined experimental mechanistic study and detailed DFT calculations clarified the crucial role of HFIP molecules in facilitating this reaction, and the unique hydrogen bond network had been deduced to account for the observed reactivity. (C) 2021 Elsevier Ltd. All rights reserved.
WOS关键词FUNCTIONALIZATION ; 2-AMINOPHENOLS ; AMIDATION ; RELEASE ; COPPER
资助项目NSFC[21877020] ; NSFC[22007020] ; Guangdong Natural Science Funds for Distinguished Young Scholar[2017A030306031] ; Natural Science Foundation of Guangdong Province[2018A030313274] ; Natural Science Foundation of Guangdong Province[2019A1515010935]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:000800222000011
出版者PERGAMON-ELSEVIER SCIENCE LTD
资助机构NSFC ; Guangdong Natural Science Funds for Distinguished Young Scholar ; Natural Science Foundation of Guangdong Province
源URL[http://ir.giec.ac.cn/handle/344007/36677]  
专题中国科学院广州能源研究所
通讯作者Gao, Hui; Zhou, Zhi; Yi, Wei
作者单位1.Guangzhou Med Univ, Sch Pharmaceut Sci, Key Lab Mol Target & Clin Pharmacol, Guangzhou 511436, Guangdong, Peoples R China
2.Guangzhou Med Univ, State Key Lab Resp Dis, Sch Pharmaceut Sci, Guangzhou 511436, Guangdong, Peoples R China
3.Guangzhou Med Univ, Affiliated Hosp 5, Guangzhou 511436, Guangdong, Peoples R China
4.Chinese Acad Sci, Guangzhou Inst Energy Convers, Guangzhou 510640, Peoples R China
推荐引用方式
GB/T 7714		 Wang, Yi,Chen, Xiaoli,Lin, Shuang,et al. Hexafluoroisopropanol (HFIP)-prompted rearrangement of N-phenoxysulfonamides for the direct assembly of ortho-sulfonamide phenols: A combined experimental and computational study[J]. TETRAHEDRON LETTERS,2022,89:5.
APA Wang, Yi.,Chen, Xiaoli.,Lin, Shuang.,Gao, Hui.,Liu, Fu-Xiaomin.,...&Yi, Wei.(2022).Hexafluoroisopropanol (HFIP)-prompted rearrangement of N-phenoxysulfonamides for the direct assembly of ortho-sulfonamide phenols: A combined experimental and computational study.TETRAHEDRON LETTERS,89,5.
MLA Wang, Yi,et al."Hexafluoroisopropanol (HFIP)-prompted rearrangement of N-phenoxysulfonamides for the direct assembly of ortho-sulfonamide phenols: A combined experimental and computational study".TETRAHEDRON LETTERS 89(2022):5.

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来源：广州能源研究所

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