31378-03-7Relevant articles and documents
Electrochemically enabled chemoselective sulfonylation and hydrazination of indoles
Zhang, Yu-Zhen,Mo, Zu-Yu,Wang, Heng-Shan,Wen, Xiao-An,Tang, Hai-Tao,Pan, Ying-Ming
, p. 3807 - 3811 (2019)
Environmentally benign electrochemically enabled chemoselective sulfonylation and hydrazination of C2,C3-unsubstituted indoles with arylsulfonyl hydrazide in the presence of ammonium bromide as a redox catalyst and electrolyte have been demonstrated in this work. Under mild electro-oxidation conditions, a series of indole hydrazination products with pharmacological activity were obtained. In vitro, the hydrazination products exhibited a better anti-cancer activity compared with the diazotization products. Further mechanistic studies showed that compound 3ae inhibits cell migration and tubulin aggregation in T-24 cells, thereby leading to cell apoptosis.
Photoredox- or Metal-Catalyzed in Situ SO2-Capture Reactions: Synthesis of β-Ketosulfones and Allylsulfones
Zheng, Min,Li, Guigen,Lu, Hongjian
, p. 1216 - 1220 (2019)
The first report of the in situ capture of the SO2 fragment of the trifluoromethylsulfonyl radical is described here. With cyclobutanone oximes as representative alkyl radical precursors, vinyl triflates and allyl trifluoromethylsulfones were employed as radical acceptors and SO2 sources to provide various β-ketosulfones and allylsulfones, known to be significant building blocks. Without the use of any additives including external SO2 gas, the reaction was performed under mild photoredox- or metal-catalytic conditions while tolerating various functional groups.
A facile one-pot synthesis of β-keto sulfones from ketones under solvent-free conditions
Kumar, Dalip,Sundaree, Swapna,Rao,Varma, Rajender S.
, p. 4197 - 4199 (2006)
An easy solvent-free method is described for the conversion of ketones into β-keto sulfones in high yields that involves the in situ generation of α-tosyloxyketones, followed by nucleophilic substitution with sodium arene sulfinate in the presence of tetra-butylammonium bromide at room temperature. The salient features of this one-pot protocol are short reaction times, cleaner reaction profiles, and simple work-up that precludes the use of toxic solvents.
Reaction of phenyl and 4-methylphenyl phenylethynyl sulfones with methyl acetoacetate
Vasin,Bolusheva, I. Yu.,Razin,Somov
, (2013)
Stereoselective anti-addition of methyl acetoacetate at the triple C≡C bond of phenyl- and 4-methylphenyl phenylethynyl sulfones in the presence of sodium hydride yields the corresponding Michael adduct containing an impurity of arylsulfonylacetophenone.
Acridine Orange Hemi(Zinc Chloride) Salt as a Lewis Acid-Photoredox Hybrid Catalyst for the Generation of α-Carbonyl Radicals
Das, Sanju,De Sarkar, Suman,Mandal, Tanumoy
supporting information, (2021/12/10)
A readily accessible organic-inorganic hybrid catalyst is reported for the reductive fragmentation of α-halocarbonyl compounds. The robust hybrid catalyst is a self-stabilizing combination of ZnCl2 Lewis acid and acridine orange as the photoactive organic dye. Mechanistic specifics of this hybrid catalyst have been studied in detail using both photophysical and electrochemical experiments. A systematic study enabled the discovery of the appropriate Lewis acid for the effective LUMO stabilization of α-halocarbonyl compounds and thereby lowering of reduction potential within the range of a standard organic dye. This strategy resolves the issues like dehalogenative hydrogenation or homo-coupling of alkyl radicals by guiding the photoredox cycle through an oxidative quenching pathway. The cooperativity between the photoactive organic dye and the Lewis acid counterparts empowers functionalization with a wide range of coupling partners through efficient and controlled generation of alkyl radicals and serves as an appropriate alternative to the expensive late transition metal-based photocatalysts. To demonstrate the application potential of this cooperative catalytic system, four different synthetic transformations of α-carbonyl bromides were explored with broad substrate scopes.
Method for preparing beta-carbonyl sulfone compound by using half-sandwich iridium complex
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Paragraph 0038-0041, (2021/07/31)
The invention relates to a method for preparing a beta-carbonyl sulfone compound by using a half-sandwich iridium complex, which comprises the following step: in the presence of alkali, by taking acetophenone and sulfonyl chloride as raw materials and taking the half-sandwich iridium complex containing an o-carboborylbenzoxazole structure as a catalyst, conducting reacting at room temperature to prepare the beta-carbonyl sulfone compound. Compared with the prior art, the method has the advantages that the half-sandwich iridium complex containing the o-carboborylbenzoxazole structure is used as the catalyst, acetophenone and sulfonyl chloride are efficiently catalyzed to react under the room temperature condition to synthesize the beta-carbonyl sulfone compound, the product yield is high, the reaction condition is mild, the substrate is cheap and easy to obtain, and the catalytic efficiency is high.