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.
Oxy-sulfonylation of terminal alkynesviaC-S coupling enabled by copper photoredox catalysis
Charpe, Vaibhav Pramod,Das, Deb Kumar,Hwang, Kuo Chu,Hwu, Jih Ru,Lin, Chun-Cheng,Pampana, V. K. K.,Sagadevan, Arunachalam
supporting information, p. 3569 - 3574 (2021/06/06)
We report the first literature example using visible light-induced trimethylsilyl azide (TMS-N3)-assisted copper-catalyzed oxy-sulfonylation of terminal C-C bonds to form β-keto sulfones (C-S bond formation). TMS-N3promotes the reaction by facilitating the formation of sulfonyl radicals, which later decompose into N2gas upon light irradiation. This method involves the use of commercially available and stable starting materials. Also, a wide range of functional groups have been well-tolerated under the current photoredox process, evading the side product formation. Potent biologically active compounds, such as CES1, 11β-HSD1 inhibitors, anti-analgesic agents, and reactive synthesis intermediates were synthesized to demonstrate the synthetic utility of the current methodology. Moreover, green chemistry metrics and Eco-scale evaluation for the current photochemical method show that the protocol is eco-friendly and highly efficient.
Chemoenzymatic Oxosulfonylation-Bioreduction Sequence for the Stereoselective Synthesis of β-Hydroxy Sulfones
González-Sabín, Javier,Gotor-Fernández, Vicente,López-Agudo, Marina,Lavandera, Iván,Ríos-Lombardía, Nicolás
, (2021/08/23)
A series of optically active β-hydroxy sulfones has been obtained through an oxosulfonylation-stereoselective reduction sequence in aqueous medium. Firstly, β-keto sulfones were synthesized from arylacetylenes and sodium sulfinates to subsequently develop the carbonyl reduction in a highly selective fashion using alcohol dehydrogenases as biocatalysts. Optimization of the chemical oxosulfonylation reaction was investigated, finding inexpensive iron(III) chloride hexahydrate (FeCl3 ? 6H2O) as the catalyst of choice. The selection of isopropanol in the alcohol-water media resulted in high compatibility with the enzymatic process for enzyme cofactor recycling purposes, providing a straightforward access to both (R)- and (S)-β-hydroxy sulfones. The practical usefulness of this transformation was illustrated by describing the synthesis of a chiral intermediate of Apremilast. Interestingly, the development of a chemoenzymatic cascade approach avoided the isolation of β-keto sulfone intermediates, which allowed the preparation of chiral β-hydroxy sulfones in high conversion values (83–94 %) and excellent optical purities (94 to >99 % ee).
