60260-74-4Relevant academic research and scientific papers
Correction: Enantioselective copper catalysed intramolecular C-H insertion reactions of α-diazo-β-keto sulfones, α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones; The influence of the carbene substituent (Organic and Biomolecular Chemistry (2017)
Shiely, Amy E.,Slattery, Catherine N.,Ford, Alan,Eccles, Kevin S.,Lawrence, Simon E.,Maguire, Anita R.
, p. 1284 - 1285 (2019)
The authors regret that there were errors in Fig. 3. Specifically, the bars representing ligands 15 and 16 were incorrectly labeled in the legend and there was an error in one of the values used to prepare the figure. The correct figure prepared using the
Photoinduced C(sp3)-H sulfination empowers the direct and chemoselective introduction of the sulfonyl group
Arman, Hadi D.,Haug, Graham C.,Jin, Shengfei,Larionov, Oleg V.,Nguyen, Viet D.,Trevino, Ramon
, p. 13914 - 13921 (2021/11/04)
Direct installation of the sulfinate group by the functionalization of unreactive aliphatic C-H bonds can provide access to most classes of organosulfur compounds, because of the central position of sulfinates as sulfonyl group linchpins. Despite the importance of the sulfonyl group in synthesis, medicine, and materials science, a direct C(sp3)-H sulfination reaction that can convert abundant aliphatic C-H bonds to sulfinates has remained elusive, due to the reactivity of sulfinates that are incompatible with typical oxidation-driven C-H functionalization approaches. We report herein a photoinduced C(sp3)-H sulfination reaction that is mediated by sodium metabisulfite and enables access to a variety of sulfinates. The reaction proceeds with high chemoselectivity and moderate to good regioselectivity, affording only monosulfination products and can be used for a solvent-controlled regiodivergent distal C(sp3)-H functionalization.
Preparation method of methyl sulfone compound
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Paragraph 0005; 0034, (2021/02/24)
The invention discloses a synthesis method of a methyl sulfone compound, which comprises the following steps: by using an iodinated compound as a substrate, adding a sulfite compound into the substrate, and using a 1, 4-dioxane solution as a solvent, heating under the protection of nitrogen under the actions of a silicon reagent, a phase transfer catalyst and a palladium catalyst to obtain a crudeproduct; then purifying the crude product, firstly filtering the crude product, and removing the solvent to obtain residues; carrying out silica gel column chromatography on the residues, leaching with eluent, and collecting effluent; combining the effluent containing the product; and concentrating the combined effluent to remove the solvent, and finally carrying out vacuum drying to obtain the target product. The method has the advantages of simple process flow, easiness in product purification, environmental safety and high yield.
Sodium Dithionite-Mediated Decarboxylative Sulfonylation: Facile Access to Tertiary Sulfones
Chen, Shihao,Jiang, Xuefeng,Li, Yaping,Wang, Ming
supporting information, p. 8907 - 8911 (2020/04/22)
A straightforward multicomponent decarboxylative cross coupling of redox-active esters (N-hydroxyphthalimide ester), sodium dithionite, and electrophiles was established to construct sterically bulky sulfones. The inorganic salt sodium dithionite not only served as the sulfur dioxide source, but also acted as an efficient radical initiator for the decarboxylation. Notably, diverse naturally abundant carboxylic acids and artificially prepared carboxyl-containing drugs with multiple heteroatoms and sensitive functional groups successfully underwent this decarboxylative sulfonylation to provide sterically bulky tertiary sulfones. Mechanistic studies further demonstrated that decarboxylation was the rate-determining step and occurred via a single-electron transfer (SET) process with the assistance of sodium dithionite.
Large-steric-hindrance alkyl-alkyl sulfone compound as well as synthesis method and application thereof
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Paragraph 0177-0181, (2020/07/24)
The invention belongs to the technical field of organic compound synthesis and application, and discloses a large-steric-hindrance alkyl-alkyl sulfone compound shown as a formula (4) and a synthesis method thereof. Carboxylic acid derived redox ester, a reducing sulfur dioxide source and an alkyl electrophilic reagent are used as raw materials, and a series of large-steric-hindrance alkyl-alkyl sulfone compounds are obtained by a three-component one-pot method. The synthesis method is wide in raw material source, cheap and easy to obtain; the reaction operation is simple; the functional grouptolerance is high; the use of a reducing sulfur dioxide source in the reaction avoids the addition of an additional equivalent metal reducing reagent, is economical and practical, and avoids the pollution of waste metals to the environment. The invention also discloses application of the alkyl-alkyl sulfone compound in preparation of drugs, pesticides, organic photoelectric materials and the like.The method has high practical value and wide application prospect.
Enantioselective copper catalysed intramolecular C-H insertion reactions of α-diazo-β-keto sulfones, α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones; the influence of the carbene substituent
Shiely, Amy E.,Slattery, Catherine N.,Ford, Alan,Eccles, Kevin S.,Lawrence, Simon E.,Maguire, Anita R.
supporting information, p. 2609 - 2628 (2017/04/01)
Enantioselectivities in C-H insertion reactions, employing the copper-bis(oxazoline)-NaBARF catalyst system, leading to cyclopentanones are highest with sulfonyl substituents on the carbene carbon, and furthermore, the impact is enhanced by increased steric demand on the sulfonyl substituent (up to 91%ee). Enantioselective intramolecular C-H insertion reactions of α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones are reported for the first time.
Aspergillus genus as a source of new catalysts for sulfide oxidation
Mascotti, Maria Laura,Orden, Alejandro A.,Bisogno, Fabricio R.,De Gonzalo, Gonzalo,Kurina-Sanz, Marcela
experimental part, p. 32 - 36 (2012/10/18)
This work extends the present knowledge about the ability of filamentous fungi to selectively transform sulfur-containing compounds. Here, it has been demonstrated that several species of the Aspergillus genus are able to perform chemo- and stereoselectiv
Enzymatic synthesis of novel chiral sulfoxides employing Baeyer-villiger monooxygenases
Rioz-Martinez, Ana,De Gonzalo, Gonzalo,Pazmino, Daniel E. Torres,Fraaije, Marco W.,Gotor, Vicente
experimental part, p. 6409 - 6416 (2011/02/24)
Optically active sulfoxides are compounds of high interest in organic chemistry. Herein, we report the preparation of a set of chiral heteroaryl alkyl, cyclohexyl alkyl, and alkyl alkyl sulfoxides by using enantioselective sulfoxidation reactions employing three Baeyer-Villiger monooxygenases (BVMOs). Careful selection of the reaction conditions, starting sulfide, and biocatalyst can be used to achieve good to excellent enantiomeric excess values. Thus, valuable chiral synthons can be obtained by performing the reactions under mild and environmentally friendly conditions. The most promising biotransformations that employ a BVMO cell-free extract preparation have been developed on a 250-mg scale to give the chiral sulfoxides in high yields in most of the reactions. Copyright
Optimization of asymmetric oxidation of sulfides with the Fe(salan) complex in water and the expanded scope of its application
Egami, Hiromichi,Katsuki, Tsutomu
experimental part, p. 1543 - 1546 (2009/04/07)
The scope of asymmetric oxidation of sulfides using Fe(salan) complex as a catalyst and aqueous hydrogen peroxide as an oxidant in water was broadened by optimizing the reaction conditions with respect to reaction temperature, catalyst loading, and amount of water solvent. The oxidation proceeded with high enantioselectivity under the optimized conditions. The undesired over-oxidation of the resultant sulfoxides was significantly suppressed and the yields of sulfoxides were improved. Various functional groups were tolerant of the conditions.
Fe(salan)-catalyzed asymmetric oxidation of sulfides with hydrogen peroxide in water
Egami, Hiromichi,Katsuki, Tsutomu
, p. 8940 - 8941 (2008/02/11)
A new chiral Fe(salan) complex was synthesized, and it was found to serve as an efficient catalyst for asymmetric oxidation of sulfides using hydrogen peroxide in water without surfactant. Not only alkyl aryl sulfides but also various methyl alkyl sulfides were oxidized to the corresponding sulfoxides with high enantioselectivities up to 96% ee. It should be noted that the turnover number of complex 4 amounts to 8000. Copyright
