68969-25-5Relevant academic research and scientific papers
Photoredox Alkenylation of Carboxylic Acids and Peptides: Synthesis of Covalent Enzyme Inhibitors
Kammer, Lisa Marie,Lipp, Benjamin,Opatz, Till
, p. 2379 - 2392 (2019/01/21)
The synthesis of vinyl sulfones and (α,β-unsaturated) nitriles from carboxylic acids was realized through oxidative decarboxylation with 1,4-dicyanoanthracene as an organic photoredox catalyst. Various types of C-radicals are generated and used to construct three different classes of potential covalent protease inhibitors. The procedure is functional group tolerant and applicable to natural products and druglike scaffolds. It may serve for the rapid construction of screening candidates as demonstrated by a three-step synthesis of the known protease inhibitor K11777.
Safe and Metal-Free Synthesis of 1-Alkenyl Aryl Sulfides and Their Sulfones from Thiiranes and Diaryliodonium Salts
Dong, Jun,Xu, Jiaxi
, p. 2407 - 2415 (2018/04/16)
A series of 1-alkenyl aryl sulfides was synthesized from thiiranes and diaryliodonium salts in tetrahydrofuran in the presence of potassium tert -butoxide. The proposed reaction mechanism involves generation of benzynes from the diaryliodonium salts in the presence of the base. Then, nucleophilic attack of the benzynes by thiiranes, followed by hydrogen abstraction and ring opening of the generated thiiranium intermediates, provides the sulfides. These sulfides were further oxidized with performic acid to the corresponding sulfones. The current method provides a metal-free and safe method for the preparation of 1-alkenyl aryl sulfides and their sulfones.
An efficient synthesis of vinyl sulfones from alkenes and aryl sulfinates
Das, Biswanath,Lingaiah, Maram,Damodar, Kongara,Bhunia, Nisith
experimental part, p. 2941 - 2944 (2011/10/19)
Vinyl sulfones have been efficiently synthesized by treatment of alkenes with sodium arene sulfinates using potassium iodide and sodium periodate in the presence of a catalytic amount of acetic acid at room temperature. The products are formed in high yie
Cross-coupling of organoboronic acids and sulfinate salts using catalytic copper(II) acetate and 1,10-phenanthroline: synthesis of aryl and alkenylsulfones
Huang, Fang,Batey, Robert A.
, p. 7667 - 7672 (2008/02/08)
A mild method for the preparation of aryl and alkenylsulfones from the cross-coupling reaction of organoboronic acids and sodium sulfinate salts is described. Optimized conditions utilize a catalytic amount of copper(II) acetate monohydrate with 1,10-phenanthroline as ligand in the presence of 4 ? molecular sieves. A co-solvent mixture of dichloromethane/DMSO was used, with reactions occurring at 40 °C under an atmosphere of oxygen. Reaction at room temperature also yields sulfone product, but in lower yields. The method tolerates a variety of substituents on the organoboronic acid, including amide, aldehyde, halide and nitro functionalities, as well as ortho-substituents. In general, the reaction is found to be less efficient using arylboronic acids bearing electron-withdrawing substituents, or using aryltrifluoroborate salts.
Asymmetric dihydroxylation of vinyl sulfones: Routes to enantioenriched α-hydroxyaldehydes and the enantioselective syntheses of furan-2(5H)-ones
Evans, Paul,Leffray, Mélanie
, p. 7973 - 7981 (2007/10/03)
The asymmetric dihydroxylation of α,β-unsaturated sulfones under Sharpless conditions affords enantioenriched α-hydroxyaldehydes in a complex mixture of dimeric species. These mixtures undergo olefination generating the corresponding α,β-unsaturated esters or furan-2(5H)-ones with high levels of enantiomeric excess. The application of this method for the rapid stereoselective synthesis of the furanone natural products; quercus lactone and maritolide, are described.
A facile regio- and stereocontrolled synthesis of (E)-disubstituted vinyl sulfones via transformation of alkenylzirconocenes with sulfonyl chlorides
Duan, De-Hui,Huang, Xian
, p. 317 - 318 (2007/10/03)
Alkenylzirconium reagents, readily obtained by hydrozirconation of terminal alkynes, can smoothly react with sulfonyl chlorides to afford (E)- disubstituted vinyl sulfones in moderate to good yields. Some γ- functionalized vinyl sulfones can be also conve
A useful method for configuration assignement of vinyl sulfides; stereochemical reassessment of the radical addition of benzenethiol to alkynes
Benati, Luisa,Capella, Laura,Montevecchi, Pier Carlo,Spagnolo, Piero
, p. 1035 - 1038 (2007/10/02)
A comparative analysis of the 1H NMR spectra of (E)- and (Z)-phenyl and alkyl sulfides and their corresponding sulfones provides a useful method for establishing their configuration.Although by employing this method we generally confirm our previous configurational assignement for benzenethiol/alkyne adducts, those for (E)- and (Z)-3-(phenylsulfanyl)hex-3-ene and 4-phenylsulfanyl)oct-4-ene, are shown to have been assigned incorrectly.In the light of the present results it is concluded that radical addition of benzenethio to alkynes at 100 deg C generally proceeds with trans-selectivity.This conclusion is the reverse of our earlier claim for the effect that benzenethiol adds to terminal alkynes and alkylphenylacetylenes in a trans-stereoselective mode, but in a cis-stereoselective mode to dialkylacetylenes bearing (rather) bulky alkyl groups.
An Indirect Method for Engaging Unactivated Alkenes as Effective Dienophiles in Regioselective Diels-Alder Reactions
Paquette, Leo A.,Crouse, Gary D.
, p. 141 - 142 (2007/10/02)
Terminal alkenes and cyclic olefins can be made to enter into efficient, regiocontrolled Diels-Alder cycloaddition by prior selenosulfonation and oxidation to the vinyl sulfone.Reductive desulfonation after condensation with an activated diene provides th
