- Practical Electro-Oxidative Sulfonylation of Phenols with Sodium Arenesulfinates Generating Arylsulfonate Esters
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A practical and sustainable synthesis of arylsulfonate esters has been developed through electro-oxidation. This reaction employed the stable and readily available phenols and sodium arenesulfinates as the starting materials and took place under mild reaction conditions without additional oxidants. A wide range of arylsulfonate esters including those bearing functional groups were produced in good to excellent yields. This reaction could also be conducted at a gram scale without a decrease of reaction efficiency. Those results well demonstrated the potential synthetic value of this reaction in organic synthesis.
- Tian, Zhibin,Gong, Qihang,Huang, Tianzeng,Liu, Long,Chen, Tieqiao
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p. 15914 - 15926
(2021/05/04)
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- Deprotection of durable benzenesulfonyl protection for phenols — efficient synthesis of polyphenols
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A robust protection method for phenol was demonstrated by the use of durable benzenesulfonyl group, which survives various harsh reaction conditions using Grignard reagent, organolithium reagent, metal alkoxide, phosgene, mineral, and Lewis acids. A facile deprotection condition utilizing pulverized KOH (5 equiv) and t-BuOH (10 equiv) in hot toluene makes this protocol as a practical method, which can be applied to the multistep synthesis of biologically and medicinally important polyphenol compounds.
- Alam, Mohammad Shariful,Koo, Sangho
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supporting information
p. 247 - 254
(2018/01/08)
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- KINETICS OF SULFONYLATION OF SUBSTITUTED PHENOLS IN THE PRESENCE OF TRIETHYLAMINE
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The rate constants for the sulfonation of meta- and para-substituted phenols by benzenesulfonyl chloride in the presence of triethylamine in benzene were determined.The dependence of the rate constants on the Hammett ? constants has a V-shaped form.The effect of the leaving group was investigated, and the kinetic isotope effect was determined.The possibility of reaction by two catalytic paths (nucleophilic and general base catalysis) is discussed, and proposals were made about the reaction mechanism.
- Vizgert, R. V.,Maksimenko, N. N.,Krut'ko, I. N.
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p. 1247 - 1252
(2007/10/02)
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