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Jintao Han Hongbo Dong Zhihong Xu Jianping Lei Mingan Wang 《International journal of molecular sciences》2013,14(6):12484-12495
The sequential sulfonylation/desulfination reactions of 5-benzylthiohydantoin with excess arylsulfonyl chlorides in the presence of triethylamine have been developed to afford a wide range of 5-arylidene thiohydantoin derivatives in moderate to excellent yields. A plausible sulfonylation/desulfination mechanism was proposed. The bioassay showed that these compounds exhibit certain fungicidal activities with the 71.9% inhibition rate of 2K against B. cinerea, and 57.6% inhibition rate of 2m against A. solani, respectively. 相似文献
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《Journal of Sulfur Chemistry》2013,34(3):197-203
Silica gel-supported aluminum chloride (SiO2–AlCl3) has been shown to be a mild, efficient, and chemoselective heterogeneous Lewis acid catalyst for direct conversion of arenes to sulfones using sulfonic acids as sulfonylating agents. The catalyst can be prepared easily with cheap starting materials and is stable (as a bench-top catalyst) and reusable. 相似文献
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Wen‐Chao Yang Peng Dai Kai Luo Lei Wu 《Advanced Synthesis \u0026amp; Catalysis》2016,358(20):3184-3190
We disclose here the first iodine/tert‐butyl hydroperoxide (I2/TBHP)‐mediated benzylic C–H sulfonylation of phenol derivatives. This new methodology provides an economic, operationally simple and metal‐free approach toward C(sp3)–S bond formation with medium to excellent yields at room temperature. Moreover, a novel sulfonylative and peroxidative bifunctionalization of phenol derivatives was also achieved by changing the amount of the oxidant. The reaction mechanism is exemplified via a radical pathway.
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Novel organic-inorganic hybrid mesoporous molecular sieve of MCM-41 type containing both bridge-bonded phenyl groups in the walls and terminally bonded phenyl groups protruding into the channel space was synthesized using TEOS, 1,4-bis(triethoxysilyl)benzene (BTESB) and (triethoxysilyl)benzene (TESB) as precursors, cetyl pyridine bromide (CPBr) as template under acidic conditions. This new material was characterized by means of FT-IR, PXRD and nitrogen adsorption-desorption isotherms. The mesoporous organosilica was in-situ sulfonylated and reacted with diamines. 相似文献
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《Journal of Sulfur Chemistry》2013,34(4):342-346
In this paper, a simple and efficient protocol for the chemoselective sulfonation of indoles using aryl sulfonyl chlorides in the presence of CuI is reported. The reaction proceeds under mild conditions and is applicable to indoles bearing a selection of functional groups without NH protection. 相似文献
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A copper‐mediated oxidative radical addition/cyclization cascade of o‐cyanoarylacrylamides with sodium trifluoromethanesulfonate (Langlois’ reagent) has been achieved. The reaction proceeds through radical addition, cyclization, and imine hydrolysis, in which the cyclization was accomplished by an intramolecular addition of the carbon radical to the nitrile. This transformation exhibits a wide substrate scope and good functional group tolerance, thus providing a highly efficient and practical access to a variety of trifluoromethylated quinoline‐2,4(1H,3H)‐diones. Furthermore, using other sulfinic acid sodium salts as sulfonylating agents, sulfonated quinolinediones were also obtained through a similar radical cascade.
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A simple and mild copper‐catalyzed sulfonylation of 8‐aminoquinolines with sodium and lithium sulfinates is reported. In the presence of manganese(III) acetate [Mn(OAc)3] as cooxidant a highly site‐selective C−H functionalization at the C‐5 position takes place. The reaction proceeds readily at room temperature in air and various sulfones were synthesized in moderate to high yields. Moreover, a straightforward procedure for the conversion of organolithium reagents and sulfur dioxide into C‐5 sulfonylated quinolines was developed.
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A comparison of the relative catalytic efficiencies of Lewis‐basic amines vs. N‐oxides for the acylation, sulfonylation and silylation of primary, secondary and tertiary alcohols is reported. Whilst the amines are generally superior to the N‐oxides for acylation, the N‐oxides are superior for sulfonylation and silylation. In particular, 1‐methylimidazole N‐oxide (NMI‐O) is found to be a highly efficient catalyst for sulfonylation and silylation reactions. To the best of our knowledge, NMI‐O is the first amine or N‐oxide Lewis basic organocatalyst capable of promoting the efficient silylation of tert‐alcohols in high yield with low catalyst loading under mild reaction conditions.