2022
DOI: 10.1021/acs.orglett.2c03421
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Sulfur-Phenolate Exchange As a Fluorine-Free Approach to S(VI) Exchange Chemistry on Sulfonyl Moieties

Abstract: SuFEx chemistry has recently evolved as next-generation click chemistry. However, in most SuFEx syntheses, additional reagents/catalysts and carefully controlled conditions are still needed. Here, we aim to further generalize S(VI) exchange chemistry, using 4-nitrophenyl phenylmethanesulfonate as example, in which the nitrophenolate group is exchanged for a wide range of (substituted) phenols and alkyl alcohols. Quantitative yields were reached within 10 min under ambient conditions and required only filtering… Show more

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Cited by 9 publications
(8 citation statements)
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“…1 H NMR analysis of the crude reaction mixture after degradation also indicated side reactions on the amine itself, though the exact products were not analyzed in detail. As the corresponding reaction with phenols showed no such dependence on the presence of water, we postulate that a reaction occurs between the deprotonated amine and water. As a result of this, the amount of amine available for reaction with 1 is decreased, causing a lower yield and eventual base-catalyzed hydrolysis of 1 .…”
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confidence: 74%
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“…1 H NMR analysis of the crude reaction mixture after degradation also indicated side reactions on the amine itself, though the exact products were not analyzed in detail. As the corresponding reaction with phenols showed no such dependence on the presence of water, we postulate that a reaction occurs between the deprotonated amine and water. As a result of this, the amount of amine available for reaction with 1 is decreased, causing a lower yield and eventual base-catalyzed hydrolysis of 1 .…”
mentioning
confidence: 74%
“… 31 , 32 Specifically, 4-nitrophenyl benzylsulfonate ( 1 ) was shown to be a good alternative to benzylsulfonyl chloride or fluoride as a starting material, by the creation of a large library of sulfonates in a near-quantitative fashion using a simple and fast SuPhenEx reaction at room temperature. 32 Now, we demonstrate that the same class of starting materials can also be used to create a large array of sulfonamides in good yields via the reaction with a wide range of alkylamines and N -alkylated anilines ( Figure 1 ).…”
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confidence: 99%
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