78974-45-5Relevant academic research and scientific papers
Synthesis of Sulfones and Sulfonamides via Sulfinate Anions: Revisiting the Utility of Thiosulfonates
Shyam, Pranab K.,Jang, Hye-Young
, p. 1761 - 1767 (2017)
Simple and high-yielding strategies for the production of a variety of sulfones and sulfonamides, using thiosulfonates synthesized by copper-catalyzed aerobic dimerization, are reported. Although thiosulfonates are an old class of compound, practical methods for their synthesis and utilization have not been rigorously developed. In this study, we revisit the reactions of easily accessible thiosulfonates to form sulfinate anions. Because of the similar reactivity of thiosulfonates and metal sulfinates derived from toxic SO2, thiosulfinates are proposed to be stable, nontoxic alternatives to metal sulfinate salts.
Base-Mediated Radical Borylation of Alkyl Sulfones
Huang, Mingming,Hu, Jiefeng,Krummenacher, Ivo,Friedrich, Alexandra,Braunschweig, Holger,Westcott, Stephen A.,Radius, Udo,Marder, Todd B.
supporting information, (2021/12/02)
A practical and direct method was developed for the production of versatile alkyl boronate esters via transition metal-free borylation of primary and secondary alkyl sulfones. The key to the success of the strategy is the use of bis(neopentyl glycolato) diboron (B2neop2), with a stoichiometric amount of base as a promoter. The practicality and industrial potential of this protocol are highlighted by its wide functional group tolerance, the late-stage modification of complex compounds, no need for further transesterification, and operational simplicity. Radical clock, radical trap experiments, and EPR studies were conducted which show that the borylation process involves radical intermediates.
Cu-mediated: vs. Cu-free selective borylation of aryl alkyl sulfones
Hu, Jiefeng,Huang, Mingming,Marder, Todd B.,Radius, Udo,Tang, Man,Westcott, Stephen A.
supporting information, p. 395 - 398 (2022/01/19)
A Cu-catalysed borylation of aryl alkyl sulfones was developed for the high yield synthesis of versatile arylboronic esters using a readily prepared NHC-Cu catalyst. In addition, the selective cleavage of either alkyl(C)-sulfonyl or aryl(C)-sulfonyl bonds
Cu2O-catalyzed C–S coupling of quaternary ammonium salts and sodium alkane-/arene-sulfinates
Chen, Hongyi,Huang, Youming,Zeng, Qingle,Zheng, Wenting
, (2020/08/28)
A new protocol for the synthesis of (enantioenriched) benzylic sulfones via the Cu2O-catalyzed C–S bond cross coupling of alkane-/arene-sulfinates and (enantioenriched) benzylic quaternary ammonium salts has been developed. The product benzylic sulfones were obtained in good to high yields (75–96%). Chiral arylmethyl sulfones with high enantiomeric excess (90–94% ee) were also synthesized in the presence of Cu2O and 1,1′-bis-(diphenylphosphino)ferrocene (dppf).
Base-controlled divergent synthesis of vinyl sulfones from (benzylsulfonyl)benzenes and paraformaldehyde
Xiao, Fuhong,Hu, Yangling,Huang, Huawen,Xu, Fen,Deng, Guo-Jun
supporting information, p. 3527 - 3535 (2020/05/25)
A tuneable metal-free protocol for the selective preparation of a-substituted vinyl sulfone and (E)-vinyl sulfone derivatives has been described. In this process, stable paraformaldehyde was used as the carbon source. The base played an important role in the selectivity control of transformations. More than 50 products were synthesized with excellent chemoselectivity and broad functional group tolerance.
Manganese-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols with Sulfones: A Tool to Access Highly Substituted Vinyl Sulfones
Barman, Milan K.,Maji, Biplab,Waiba, Satyadeep
, p. 973 - 982 (2021/08/24)
The development of first-row-transition-metal catalysts that can match with the reactivities of the noble metals is considered to be challenging yet very much a desirable goal in homogeneous catalysis. It has become even more fascinating to develop processes where these metals show a unique reactivity and selectivity than their higher congeners. Herein, we report on the catalytic activity of a pincer complex of the abundant earth metal manganese for an unprecedented acceptorless dehydrogenative coupling of alkyl sulfones with alcohols. Thus, highly functionalized vinyl sulfones were obtained in moderate to good yields. Both benzylic and aliphatic alcohols could be utilized, and several functional groups including bromides and iodides are tolerated under the reaction conditions. The reaction is environmentally benign, producing dihydrogen and water as byproducts. Preliminary mechanistic experiments involving kinetic, deuterium-labeling, and NMR experiments were performed.
Reusable BNPs-SiO2@(CH2)3NHSO3H-catalysed selective oxidation of sulfides to sulfones
Bahrami, Kiumars,Khodamorady, Minoo
, (2018/10/15)
Reusable boehmite nanoparticles–silica–NHSO3H (BNPs-SiO2@(CH2)3NHSO3H) was found to be an efficient heterogeneous nanocatalyst for the selective oxidation of sulfides to sulfones in the presence of H2O2. Excellent yields, easy and quick isolation of products, short reaction times and excellent selectivity are the main advantages of this method. The catalyst was characterized using Fourier transform infrared spectroscopy, energy-dispersive X-ray analysis, X-ray diffraction, and transmission and scanning electron microscopies.
MANUFACTURING METHOD OF COMPOUND HAVING SULFONYL GROUP
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Paragraph 0108; 0109; 0121-0124, (2018/10/03)
The present invention relates to a method for manufacturing a compound having a sulfonyl group, which includes a step for reacting thiosulfonates in a solvent comprising nucleophilic bases with an electrophilic agent. Accordingly, the present invention can manufacture the compound having the sulfonyl group with a variety of structures with high efficiency and high yield through more simplified processes than conventional methods.COPYRIGHT KIPO 2018
Arylative Desulfonation of Diarylmethyl Phenyl Sulfone with Arenes Catalyzed by Scandium Triflate
Nambo, Masakazu,Ariki, Zachary T.,Canseco-Gonzalez, Daniel,Beattie, D. Dawson,Crudden, Cathleen M.
supporting information, p. 2339 - 2342 (2016/06/09)
A scandium-triflate-catalyzed arylative desulfonation of diarylmethyl phenyl sulfones with arenes and heteroarenes was established. A variety of both sulfone and arene substrates were reacted to afford symmetric and nonsymmetric triarylmethanes in good yields. Further transformations of the resulting triarylmethanes and application to the concise synthesis of a bactericidal agent analogue were also demonstrated.
Modular synthesis of triarylmethanes through palladium-catalyzed sequential arylation of methyl phenyl sulfone
Nambo, Masakazu,Crudden, Cathleen M.
supporting information, p. 742 - 746 (2014/01/23)
Triarylmethanes, which are valuable structures in materials, sensing and pharmaceuticals, have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium-catalyzed C-H arylation reactions, followed by an arylative desulfonation. This method provides a new synthetic approach to multisubstituted triarylmethanes using readily available haloarenes and aryl boronic acids, and is also valuable for the preparation of unexplored triarylmethane-based materials and pharmaceuticals. Unsymmetric triarylmethanes have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium-catalyzed C-H arylation reactions, followed by an arylative desulfonation. Copyright
