- Direct synthesis of sulfinic esters via ultrasound accelerated tandem reaction of thiols and alcohols with N-bromosuccinimide
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The direct transformation of various thiols and simple alcohols with N-bromosuccinimide into sulfinic esters has been investigated by using different categories of base/acidic catalysts as well as co-solvents under varied reaction conditions. The reaction was found out to afford the sulfinic esters with high yields in the absence of catalysts, especially within the shorter time under the acceleration of ultrasonic irradiation than under the longer-lasting conventional stirring conditions.
- Nguyen, Lan-Anh Thi,Le, Tri-Nghia,Duong, Cong-Thang,Vo, Chi-Tam,Duus, Fritz,Luu, Thi Xuan Thi
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p. 519 - 528
(2021/05/27)
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- Intramolecular Homolytic Substitution Enabled by Photoredox Catalysis: Sulfur, Phosphorus, and Silicon Heterocycle Synthesis from Aryl Halides
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Aryl radical generation and manipulation constitutes a long-standing challenge in organic synthesis. Photocatalytic single-electron reduction of aryl halides has been established as a premier activation pathway to reach these intermediates. The current st
- Garrido-Castro, Alberto F.,Salaverri, Noelia,Maestro, M. Carmen,Alemán, José
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supporting information
p. 5295 - 5300
(2019/07/03)
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- Regiospecific alkyl addition of (hetero)arene-fused thiophenes enabled by a visible-light-mediated photocatalytic desulfuration approach
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A photoredox-mediated, regiospecific alkyl addition reaction of (hetero)arene-fused thiophenes has been developed, employing bench-stable N-benzoyl alkyl-sulfinamides as the alkyl sources. This protocol offers a unique desulfuration approach to generate a
- Di, Jiamei,He, Huan,Wang, Falu,Xue, Fei,Liu, Xiao-Yu,Qin, Yong
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supporting information
p. 4692 - 4695
(2018/05/22)
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- A Desulfurative Strategy for the Generation of Alkyl Radicals Enabled by Visible-Light Photoredox Catalysis
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Herein, we present a new desulfurative method for generating primary, secondary, and tertiary alkyl radicals through visible-light photoredox catalysis. A process that involves the generation of N-centered radicals from sulfinamide intermediates, followed by subsequent fragmentation, is critical to forming the corresponding alkyl radical species. This strategy has been successfully applied to conjugate addition reactions that features mild reaction conditions, broad substrate scope (>60 examples), and good functional-group tolerance.
- Xue, Fei,Wang, Falu,Liu, Jiazhen,Di, Jiamei,Liao, Qi,Lu, Huifang,Zhu, Min,He, Liping,He, Huan,Zhang, Dan,Song, Hao,Liu, Xiao-Yu,Qin, Yong
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supporting information
p. 6667 - 6671
(2018/06/11)
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- SULFINIC ACIDS AND RELATED COMPOUNDS. 21. PREPARATION OF CRYSTALLINE SULFINIC ESTERS
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In a search for means of preparing stable crystalline esters of sulfinic acids, yields from p-toluenesulfinic acid as a model were 53-92 percent with 1,1'-carbonyldiimidazole (CDI, 2) as a coupling reagent for a variety of alcohols.The best coupling reagents were CDI and chlorotrimethylsilane (16).The agent 16 could be used with sulfinate salts, as could CDI with in situ acidification.The best alcohols were 1-adamantanol and p-nitrobenzyl alcohol.Among alkanesulfinic esters, methanesulfinates were unstable oils obtainable only in low yields, but 1-butanesulfinates were obtained in 52-56 percent yield (although still as oils).As a stable disulfinic acid, 1,4-butanedisulfinic acid gave a nicely crystalline di-1-adamantyl ester (mp 123-125 deg C), but another alkanedisulfinate salt or acid that contained a disulfide moiety gave no diester by use either of 2 or 16.Key words: 1,1'-Carbonyldiimidazole, chlorotrimethylsilane, sulfinic acids, sulfinic acid esters, sulfinic acid salts, p-toluenesulfinic acid.
- Lee, Chew,Field, Lamar
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- A CONVENIENT PREPARATION OF SULPHINIC ESTERS FROM SULPHINYL CHLORIDES AND CHLOROSULPHITES USING HEXAMETHYLDISILOXANE AS CHLORIDE ANION ACCEPTOR
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Sulphinic esters can be obtained in high yields by the reaction of sulphinyl chlorides with chlorosulphites in the presence of hexamethyldisiloxane and catalytic amount of dimethyl sulphoxide.
- Drabowicz, Jozef
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p. 1753 - 1754
(2007/10/02)
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