59059-70-0Relevant articles and documents
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.
Copper(i)-catalyzed sulfonylative Suzuki-Miyaura cross-coupling
Chen, Yiding,Willis, Michael C.
, p. 3249 - 3253 (2017/04/04)
Using a simple copper(i) catalyst has allowed a high yielding sulfonylative-Suzuki-Miyaura cross-coupling reaction to be developed. The process provides a single step route to diaryl sulfones from the direct combination of aryl boronic acids, sulfur dioxide and aryl iodides, and represents the first sulfonylative variant of a classic cross-coupling reaction. Sulfur dioxide is delivered from the surrogate reagent, DABSO. Variation of the reaction conditions allowed interruption of the sulfonylative-Suzuki coupling, resulting in the formation of a presumed Cu-sulfinate intermediate. These sulfinates could be trapped as their sodium salts and treated with electrophiles to allow access to arylalkyl sulfones, β-hydroxyl sulfones, sulfonamides and sulfonyl fluorides.
Iodosulfonation of alkenes with benzenesulfinic acid - N-iodosuccinimide - Facile preparation of αβ-unsaturated sulfones
Wolff, Russell R.,Basava, Vikram,Giuliano, Robert M.,Boyko, Walter J.,Schauble, J. Herman
, p. 667 - 675 (2007/10/03)
Reaction of alkenes and alkenols with N-iodosuccinimide (NIS) and benzenesulfinic acid in dichloromethane at room temperature affords vic-iodophenylsulfonyl adducts in good to high yields. Treatment of the iodosulfones with neutral alumina in dichlorometh
Novel Versatile Synthesis of Substituted Tetrabenzoporphyrins
Finikova, Olga S.,Cheprakov, Andrei V.,Beletskaya, Irina P.,Carroll, Patrick J.,Vinogradov, Sergei A.
, p. 522 - 535 (2007/10/03)
A novel general synthetic route to tetraaryltetrabenzoporphyrins (Ar 4TBP) with various peripheral functional groups is developed. The procedure includes (i) Barton-Zard condensation of 1-nitro- or 1-phenylsulfonylcyclohexenes with isocyanoacet
Phenylsulfonyl as a β participating group
Lambert, Joseph B.,Beadle, Beth M.,Kuang, Kuiyang
, p. 9241 - 9246 (2007/10/03)
The phenylsulfonyl group (PhSQ2) has been examined for its β effect properties. The stereochemical relationship was varied between phenylsulfonyl and a nucleophilic leaving group (nucleofuge) separated by two carbons. Mechanisms were distinguished through solvent effects on rates and products. When the stereochemistry between the two groups was gauche, the only effect of phenylsulfonyl was strong inductive retardation in a mechanism involving solvent participation. With the antiperiplanar stereochemistry, however, the mechanism clearly changed to carbocation formation with a small kinetic acceleration. Thus, phenylsulfonyl is a weak β effect substituent. This remarkable property for a strongly electron-withdrawing group occurs most likely through hyperconjugation or possibly through anchimeric assistance.
Highly Stereoselective Nucleophilic Epoxidation of Simple Vinyl Sulfoxides
Fernández De La Pradilla, Roberto,Castro, Sonia,Manzano, Pilar,Martín-Ortega, María,Priego, Julián,Viso, Alma,Rodríguez, Ana,Fonseca, Isabel
, p. 4954 - 4966 (2007/10/03)
The nucleophilic epoxidation of readily available vinyl and dienyl sulfoxides with MOO-t-Bu (M = Li, Na, K) takes place in good yields, with complete preservation of double bond geometry in most cases and with moderate to excellent diastereofacial selectivity to produce enantio- and diastereomerically pure α,β-epoxy sulfoxides, valuable synthetic intermediates. Subsequent straightforward oxidation at sulfur affords the corresponding enantiopure sulfonyl oxiranes. For (1E)-2-sulfinyl dienes, the facial selectivity of this novel process may be controlled by the choice of metal (Li vs Na).
Tetra-n-butylammonium Oxone. Oxidations under Anhydrous Conditions
Trost, Barry M.,Braslau, Rebecca
, p. 532 - 537 (2007/10/02)
Tetra-n-butylammonium Oxone, readily prepared as a white solid from commercially available Oxone, performs oxidations in anhydrous methylene chloride.Under these conditions, sulfides are oxidized to sulfones in the presence of amines, ketones, esters, car
The Arenesulphonomercuriation of Alkenes - a Route to Vinyl Sulphones
Sas, Wojciech
, p. 862 - 863 (2007/10/02)
Vinyl sulphones were obtained from the reaction of alkenes with mercury(II) chloride and sodium arenesulphinate followed by base catalysed eliminative demercuriation.
ORGANIC SYNTHESIS WITH SULFONES XXXII. A CONVENIENT ROUTE TO α,β-UNSATURATED SULFONES FROM SATURATED SULFONE
Baudin, Jean-Bernard,Julia, Marc,Rolando, Christian,Verpeaux, Jean-Noel
, p. 3203 - 3204 (2007/10/02)
α-sulfonyl lithiated anions are oxidized by cupric carboxylates into α,β-unsaturated sulfones.Primary sulfones lead to pure trans-vinylic sulfones.
