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

doi:10.1016/j.tetlet.2021.153601

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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
	Wang, Yi 1,2,3; Chen, Xiaoli 4; Lin, Shuang 1,2,3; Gao, Hui 1,2,3; Liu, Fu-Xiaomin 1,2,3; Zhou, Zhi 1,2,3; Yi, Wei 1,2,3
	2022-01-19
发表期刊	TETRAHEDRON LETTERS
ISSN	0040-4039
卷号	89 页码:5
通讯作者	Gao, Hui(gaoh9@gzhmu.edu.cn) ; Zhou, Zhi(zhouzhi@gzhmu.edu.cn) ; Yi, Wei(yiwei@gzhmu.edu.cn)
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.
关键词	N-phenoxysulfonamides Ortho-sulfonamide phenols Rearrangement Hexafluoroisopropanol DFT calculations
DOI	10.1016/j.tetlet.2021.153601
关键词[WOS]	FUNCTIONALIZATION ; 2-AMINOPHENOLS ; AMIDATION ; RELEASE ; COPPER
收录类别	SCI
语种	英语
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
项目资助者	NSFC ; Guangdong Natural Science Funds for Distinguished Young Scholar ; Natural Science Foundation of Guangdong Province
WOS类目	Chemistry, Organic
WOS记录号	WOS:000800222000011
出版者	PERGAMON-ELSEVIER SCIENCE LTD
引用统计
文献类型	期刊论文
条目标识符	http://ir.giec.ac.cn/handle/344007/36678
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.