6079-56-7Relevant academic research and scientific papers
Sulfinates from Amines: A Radical Approach to Alkyl Sulfonyl Derivatives via Donor-Acceptor Activation of Pyridinium Salts
Andrews, Jonathan A.,Pantaine, Lo?c R. E.,Palmer, Christopher F.,Poole, Darren L.,Willis, Michael C.
supporting information, p. 8488 - 8493 (2021/11/01)
Synthetically versatile alkyl sulfinates can be prepared from readily available amines, using Katritzky pyridinium salt intermediates. In a catalyst-free procedure, primary, secondary, and benzylic alkyl radicals are generated by photoinduced or thermally induced single-electron transfer (SET) from an electron donor-acceptor (EDA) complex, and trapped by SO2 to generate sulfonyl radicals. Hydrogen atom transfer (HAT) from Hantzsch ester gives alkyl sulfinate products, which are used to prepare a selection of medicinal chemistry relevant sulfonyl-containing motifs.
General sulfone construction: Via sulfur dioxide surrogate control
Chen, Shihao,Li, Yaping,Wang, Ming,Jiang, Xuefeng
supporting information, p. 322 - 326 (2020/02/13)
A highly efficient one-step synthesis of alkyl-alkyl and aryl-alkyl sulfones with a facile combination of halides, sulfur dioxide surrogates and phosphate esters is described. When thiourea dioxide was employed as a reductive sulfur dioxide surrogate, alkyl-alkyl sulfones were obtained under transition metal free conditions. Aryl-alkyl sulfones were obtained with an extremely low catalytic loading (0.2 mol%) via altering the mask of sulfur dioxide surrogates to sodium dithionite. A phosphate ester was employed as a stable and readily available alkyl source. Notably, this protocol has been applied to the late-stage modification of natural products and bioactive molecules.
Benzothiazole Sulfinate: A Sulfinic Acid Transfer Reagent under Oxidation-Free Conditions
Day, Jacob J.,Neill, Deshka L.,Xu, Shi,Xian, Ming
, p. 3819 - 3822 (2017/07/26)
Sulfinic acids are commonly encountered intermediates found in natural product synthesis and medicinal chemistry. However, because of high reactivity, instability, and harsh reaction conditions, they are difficult to synthesize. Herein we have developed an oxidation-free method to produce sulfinic acids and sulfinate salts using 2-sulfinyl benzothiazole (BTS). We have also demonstrated the synthetic usefulness by developing one-pot syntheses of sulfones and sulfonamides.
Synthesis of arylethyl (E)-styrylsulfones and arylsulfones by one-pot DIBAL-H/NaH-mediated reaction of β-ketosulfones
Chang, Meng-Yang,Chen, Yi-Chia,Chan, Chieh-Kai
, p. 1739 - 1744 (2014/08/05)
A facile one-pot synthetic route for preparing a series of arylethyl (E)-styrylsulfones or arylethyl arylsulfones is developed. The efficient one-pot DIBAL-H/NaH-mediated route includes reduction of α-benzyl-β- arylketosulfones and retroaldol/aldol or retro aldol reaction of the resulting intermediate. The DIBAL-H/NaH-mediated reaction mechanism has been discussed. Georg Thieme Verlag Stuttgart. New York.
Oxidations catalyzed by phenylacetone monooxygenase from Thermobifida fusca
De Gonzalo, Gonzalo,Torres Pazmino, Daniel E.,Ottolina, Gianluca,Fraaije, Marco W.,Carrea, Giacomo
, p. 3077 - 3083 (2007/10/03)
Several organic sulfides, ketones and other organic systems have been tested as substrates in oxidation reactions catalyzed by the recently discovered phenylacetone monooxygenase from Thermobifida fusca. The biocatalytic properties of this Baeyer-Villiger monooxygenase have been studied, revealing reactivity with a large range of sulfides and ketones. Oxidations of several sulfoxides, an amine and an organoboron compound were also observed. The enzyme is able to oxidize a number of sulfides with excellent enantioselectivity, demonstrating the catalytic potential of this novel biocatalyst.
Ei elimination: An unprecedented facet of sulfone chemistry
Cubbage, Jerry W.,Vos, Brian W.,Jenks, William S.
, p. 4968 - 4971 (2007/10/03)
Thermolysis of methyl 3-phenylpropyl sulfone in the gas phase results in formation of allylbenzene. Activation parameters of ΔH(+) = 53.5 ± 1.0 kcal/mol and ΔS(+) = -0.7 ± 1.4 cal/(mol·K) were obtained over the range of 490-550 °C. Similar measurements with a deuterated analogue show a substantial isotope effect, and a lower activation enthalpy is observed for the formation of styrene from methyl 2-phenylethyl sulfone. Along with high- quality ab initio calculations of activation parameters and kinetic isotope effects, these results indicate that this is the first reported Ei reaction of a simple sulfone.
New Synthetic Methods, 7. - β-Ketosulfones, Useful Ethylenediide Equivalents for the Preparation of Olefins and the Synthesis of 6-Nonen-1-ol, the Sex Attractant of the Mediterranean Fruit Fly (Ceratitus capitata)
Scholz, Dieter
, p. 98 - 106 (2007/10/02)
β-Ketosulfones, which form dianions (α and γ position), are alkylated in both positions.Brominating cleavage gives α-bromosulfones which, by Ramberg-Baecklund rearrangement, form olefins.The synthesis of 6-nonen-1-ol, starting from 2-(methylsulfonyl)cyclohexanone, is described.
