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Dehydroxylative Sulfonylation of Alcohols

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成果类型:
期刊论文
作者:
Xiang, Yi-Jun;Liu, Shun;Zhou, Jing;Lin, Jin-Hong;Yao, Xu;...
通讯作者:
Lin, Jin-Hong(jlin@sioc.ac.cn);Yao, Xu(355938360@qq.com);Xiao, Ji-Chang(jchxiao@sioc.ac.cn)
作者机构:
[Zhou, Jing; Yao, Xu; Xiang, Yi-Jun; Liu, Shun] Univ South China, Inst Pharm & Pharmacol, Hunan Prov Key Lab Tumor Microenvironm Respons Dru, Hengyang 421001, Peoples R China.
[Lin, Jin-Hong; Xiao, Ji-Chang; Xiang, Yi-Jun] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China.
[Lin, Jin-Hong] Shanghai Univ, Innovat Drug Res Ctr, Dept Chem, Shanghai 200444, Peoples R China.
通讯机构:
[Jin-Hong Lin; Ji-Chang Xiao] K
[Xu Yao] I
Institute of Pharmacy and Pharmacology, Hunan Provincial Key Laboratory of Tumor Microenvironment Responsive Drug Research, University of South China, 421001 Hengyang, PR China<&wdkj&>Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, 200032 Shanghai, PR China<&wdkj&>Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, 200032 Shanghai, PR China<&wdkj&>Department of Chemistry, Innovative Drug Research Center, Shanghai University, 200444 Shanghai, PR China
语种:
英文
关键词:
Organic compounds;Alkyl alcohols;Allyl alcohols;Benzyl alcohol;Higher yield;Pharmaceutical chemistry;Propargyl alcohol;Protocol cans;Sulfinates;Sulfonyl groups;Sulfonylation;Chemical reactions;(3 phenylprop 2 ynylsulfonyl)benzene;1 (cinnamylsulfonyl) 4 nitrobenzene;1 bromo 4 [1 [(trifluoromethyl)sulfonyl]ethyl]benzene;1 bromo 4 [[(4 trifluoromethyl)sulfonyl]methyl]benzene;1 chloro 4 (cinnamylsulfonyl)benzene;1 chloro 4 [(3 phenylprop 2 yn 1 yl)sulfonyl]benzene;1 chloro 4 [(4 phenylbutyl)sulfonyl]benzene;1 iodo 2 [[(trifluoromethyl)sulfonyl]methyl]benzene;1 methoxy 3 [(phenylsulfonyl)methyl]benzene;1 methoxy 3 [[(trifluoromethyl)sulfonyl]methyl]benzene;1 [[(difluoromethyl)sulfonyl]methyl] 3 methoxybenzene;1,3 dichloro 2 [[(trifluoromethyl)sulfonyl]methyl]benzene;1,3,5 trimethyl 2 [[(trifluoromethyl)sulfonyl]methyl]benzene;2 [1 [(trifluoromethyl)sulfonyl]ethyl]naphthalene;2 [[(difluoromethyl)sulfonyl]methyl]benzo[b]thiophene;2 [[(trifluoromethyl)sulfonyl]methyl]benzofuran;2 [[(trifluoromethyl)sulfonyl]methyl]benzo[b]thiophene;2,3 dimethoxy 5 methyl 6 [10 (phenylsulfonyl)decyl]cyclohexa 2,5 diene 1,4 dione;2,3 dimethoxy 5 methyl 6 [10 [(trifluoromethyl)sulfonyl]decyl]cyclohexa 2,5 diene 1,4 dione;4 (methoxycarbonyl)benzyl phenyl sulfone;4 (methoxycarbonyl)benzyl triflone;4 (tosylmethyl) 1,1' biphenyl;4 trifluoromethylphenylmethyl trifluoromethyl sulfone;4 [(cyclopropylsulfonyl)methyl] 1,1' biphenyl;4 [(phenylsulfonyl)methyl] 1,1' biphenyl;4 [[(4 chlorophenyl)sulfonyl]methyl] 1,1' biphenyl;4 [[(4 nitrophenyl)sulfonyl]methyl] 1,1' biphenyl;4 [[(difluoromethyl)sulfonyl]methyl] 1,1' biphenyl;4 [[(trifluoromethyl)sulfonyl]methyl] 1,1' biphenyl;5 [[(trifluoromethyl)sulfonyl]methyl]benzo[d][1,3]dioxole;alcohol derivative;chloro 4 (undec 10 en 1 ylsulfonyl)benzene;cinnamylsulfonylbenzene;methyl 4 [[(difluoromethyl)sulfonyl]methyl]benzoate;n [4 (4 fluorophenyl) 6 isopropyl 5 [[(trifluoromethyl)sulfonyl]methyl]pyrimidin 2 yl] n methylmethanesulfonamide;sulfone derivative;unclassified drug;[(4 phenylbutyl)sulfonyl]benzene;[3 (cyclopropylsulfonyl)prop 1 en 1 yl]benzene;[3 (cyclopropylsulfonyl)prop 1 yn 1 yl]benzene;[3 (trifluoromethyl)sulfonyl]prop 1 en 1 yl)benzene;[3 [(difluoromethyl)sulfonyl]prop 1 en 1 yl]benzene;[4 [(trifluoromethyl)sulfonyl]butyl]benzene;Article;controlled study;dehydroxylative sulfonylation;electrophilicity;hydroxylation;medicinal chemistry;nuclear magnetic resonance spectroscopy;nucleophilicity;racemization;reaction analysis;reaction optimization;reaction temperature;reaction time
期刊:
JOURNAL OF ORGANIC CHEMISTRY
ISSN:
0022-3263
年:
2023
卷:
88
期:
7
页码:
4818-4828
基金类别:
We thank the National Key Research and Development Program of China (2021YFF0701700), the National Natural Science Foundation (21971252, 21991122, 22271181), the Science and Technology Commission of Shanghai Municipality (22ZR1423600), the Laboratory of Tea and Health of Hengyang (202150083704), and the Undergraduate Research Learning and Innovative Experiment Project (X202110555464, 220XCX105, 220XCX310, 220XCX294, S202110555237, S202110555248, X202110555454) for financial support.
机构署名:
本校为第一机构
院系归属:
药学与生物科学学院
摘要:
Described here is the R3P/ICH2CH2I-promoted dehydroxylative sulfonylation of alcohols with a variety of sulfinates. In contrast to previous dehydroxylative sulfonylation methods, which are usually limited to active alcohols, such as benzyl, allyl, and propargyl alcohols, our protocol can be extended to both active and inactive alcohols (alkyl alcohols). Various sulfonyl groups can be incorporated, such as CF3SO2 and HCF2SO2, which are fluorinated groups of interest in pharmaceutical chemistry and the installation of which has received increasin...

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