112863-50-0

Upstream product

• 108-85-0 1-bromocyclohexane 
• 88486-41-3 1-(tri-n-butylstannyl)-2-(phenylsulfonyl)ethene 
• 112863-49-7 Thiocarbonic acid O-cyclohexyl ester O-phenyl ester 
• 38238-75-4 (E)-2-chloroethenyl phenyl sulfone 
• 56069-39-7 diethyl phenylsulfonylmethylphosphonate 
• 2043-61-0 cyclohexanecarbaldehyde 
• 626-62-0 Cyclohexyl iodide 
• 963-16-6 (E)-1,2-bis(phenylsulfonyl)ethylene 
• 110-82-7 cyclohexane 
• 1735-17-7 Cyclohexane-d12 
• 3112-85-4 methylphenylsulfonate 
• 110-83-8 cyclohexene 
• 86653-05-6 1-cyclohexyl-2-(phenylsulfonyl)ethan-1-ol 
• 58202-75-8 trans β-iodovinyl phenyl sulfone 

Downstream Products

• 218933-97-2 (2R,2'S)-2-cyclohexyl-2-[(2'-(methoxymethyl)pyrrolidin-1'-yl)amino]ethyl phenyl sulfone 
• 86653-05-6 1-cyclohexyl-2-(phenylsulfonyl)ethan-1-ol 
• 221344-99-6 (R)-2-amino-2-cyclohexylethyl phenyl sulfone 

Relevant academic research and scientific papers

Photochemically induced radical alkenylation of C(sp3)-H bonds

The direct alkenylation of C(sp3)-H bonds was achieved by employing benzophenone and 1,2-bis(phenylsulfonyl)ethylene under photo-irradiation conditions. This simple metal-free reaction enables the substitution of heteroatom-substituted methine, methylene and aliphatic C(sp3)-H bonds by (E)-sulfonylalkene units in a highly chemoselective manner. The derived sulfonylalkenes were further converted in a single step to the prenyl derivatives via a second photo-induced radical substitution and to the pyrrole derivatives via cyclization and aromatization steps. The present protocol thus serves as an efficient method for the direct extension of carbon skeletons for the synthesis of structurally complex natural products and pharmaceuticals. This journal is

Boronic Acid Mediated Carbocyanation of Olefins and Vinylation of Alkyl Iodides

Phenylboronic acid was shown to mediate the multicomponent free-radical carbocyanation of olefins and the addition of alkyl iodides to vinylsulfones. The reaction of the boronic acid with di-tert-butyl hyponitrite generates an aryl radical, which can sele

Palladium/Light induced radical alkenylation and allylation of alkyl iodides using alkenyl and allylic sulfones

Alkenylation and allylation of alkyl iodides with alkenyl and allyl sulfones, respectively, took place under Pd/photoirradiation system. The initial alkyl radical, derived from a single electron transfer between Pd(0) and RI, underwent the title transformations. Pd(0) was regenerated through a reductive elimination of PhSO2PdI, which is formed by the combination of the sulfonyl radical and the palladium radical. The addition of water was effective, presumably by pushing the equilibrium through hydrolysis of PhSO2I.

Stereoselective Synthesis of Z-α,β-Unsaturated Sulfones Using Peterson Reagents

New Peterson reagents were prepared by introducing alkyloxy groups on the silicon atom in order to fix the conformation of the sulfone anion. The reagents 1d and 1e reacted with a variety of aldehydes after the treatment with Li-base to give Z-α,β-unsaturated sulfones with up to >99:1 selectivity in good to excellent yields. For the reaction with aliphatic aldehydes, CPME (cyclopentyl methyl ether) is the choice of solvent, while DME (1,2-dimethoxyethane) gave higher selectivity for the reaction with aromatic aldehydes.

Radical-mediated thiodesulfonylation of the vinyl sulfones: access to (α-fluoro)vinyl sulfides

Radical-mediated thiodesulfonylation of the vinyl and (α-fluoro)vinyl sulfones, derived from aldehydes and ketones, with aryl thiols in organic or aqueous medium provided access to vinyl and (α-fluoro)vinyl sulfides. The vinyl sulfides were formed predominantly with E stereochemistry independent of the stereochemistry of the starting vinyl sulfones.

Radical-mediated alkenylation, alkynylation, methanimination, and cyanation of B-alkylcatecholboranes

(Chemical Equation Presented) Radical connection: Organoboranes, prepared in situ from hydroboration of olefins with catecholborane, undergo efficient coupling reactions with vinyl and alkynyl sulfones through a radical mechanism. This procedure was also

Palladium-catalyzed cascade reaction of α,β-unsaturated sulfones with aryl iodides

Unlike traditionally used acyclic 1,2-disubstituted alkenes, the reaction of α,β-unsaturated phenyl sulfones with aryl iodides under Heck reaction conditions (Pd(OAc)2 as catalyst, Ag2-CO3 as base in DMF at 120°C) takes place mainly by a cascade process, involving one unit of the alkene and three units of the aryl iodide, to afford a substituted 9-phenylsulfonyl-9,10-dihydrophenanthrene, The dominant formation of this 3:1 coupling product, instead of the Heck trisubstituted olefin, shows that aromatic C-H activation processes can compete with the usually fast syn β-hydrogen elimination step in the Heck arylation of an acyclic olefin. The structural scope of this palladium-catalyzed cascade arylation of α,β-unsaturated sulfones has proved to be wide with regard to substitution at the β-position (alkyl, aryl, or alkenyl substitution), substitution at the sulfone unit (alkyl or phenyl sulfones), and configuration at the C=C bond (trans or cis). Moreover, although less favored than in the case of the arylation of α,β-unsaturated sulfones, similarly substituted 9,10-dihydrophenanthrenes have also been obtained in the case of α,β-unsaturated phosphine oxides and α,β-unsaturated phosphonate esters. A Pd0-pdII-pdIV mechanistic pathway involving the successive formation of highly electrophilic σ-alkylpalladium intermediates and palladacycles is proposed for this multi-component arylation.

Highly stereoselective preparation of nitro olefins and nitro dienes by the addition-elimination of copper-zinc organometallics to β-alkylthio and β-phenylsulfonyl nitro olefins

The addition-elimination of copper-zinc organometallics RCu(CN)ZnX to (E)-1-nitro-2-phenylsulfonyl ethylene 2a gave highly functionalized pure (E) nitro olefins and stereoselectively (1E, 3E) and (1E, 3Z)-1-nitrodienes in excellent yields. β-Alkylthio nit

STEREOSELECTIVE ONE-POT SYNTHESIS OF VINYL SULFONES FROM METHYL PHENYL SULFONE

Vinyl sulfones are stereoselectively prepared in high yields in one-pot by the Wittig-Horner reaction via phosphorylation of methyl phenyl sulfone at low temperature.

Reactions of Alkylmercurials with Heteroatom-Centered Acceptor Radicals

The relative reactivities of alkylmercury halides toward PhS., PhSe., or I. decrease drastically from R = tert-butyl to R = sec-alkyl to R = n-butyl, indicative that R. is formed in the rate-determining step in the attack of these radicals upon RHgCl.The alkyl radicals thus formed will enter into chain reactions in which a heteroatom-centered radical (A.) is regenerated from substrates such as RS-SR, ArSe-SeAr, ArTe-TeAr, PhSe-SO2Ar, Cl-SO2Ph; ZCH=CHA (A = Cl, I, SPh, SO2Ph); or PhCCHA (A = I, SPh, SO2Ph). β-Styrenyl (PhCH=CHA, Ph2C=CHA) and β-phenethynyl (PhCCA) systems with A = I, Br, SO2Ph also enter into chain reactions with mercury(II) salts with the ligands PhS, PhSe, PhSO2, or (EtO)2PO.The relative reactivities of a series of reagents toward t-Bu. and of PhCH=CHA, Ph2C=CHA, and PhCCA toward c-C6H11. are reported as well as the regioselectivity of t-Bu. attack observed for 1,2-disubstituted ethylenes (ZCH=CHA) with Z and A from the group Ph, Cl, Br, I, SO2Ph, SPh, Bu3Sn.Reactions of (E)- and (Z)-PhCH=CHI or MeO2CCH=CHI with t-Bu. or c-C6H11. occurred in a regioselective and stereospecific (retention) manner.Reactions of (E)- and (Z)-ClCH=CHCl occurred in a nonstereospecific manner in which the E/Z product ratio increased with the bulk of the attacking radical.A similar effect on the E/Z product ratios was observed for (Z)-MeO2CCH=CHCl.