93297-04-2

Upstream product

• 42474-21-5 1,2-dibromoheptane 
• 873-55-2 sodium benzenesulfonate 
• 66-25-1 hexanal 
• 52075-21-5 phenyl heptyl sulfone 
• 3112-85-4 methylphenylsulfonate 
• 592-76-7 1-Heptene 
• 69164-56-3 (+/-)-1-(Phenylsulfonyl)-heptan-2-ol 

Relevant academic research and scientific papers

An economical and convenient synthesis of vinyl sulfones

A general process for the efficient synthesis of vinyl sulfones has been developed using commercially available sulfinic acid sodium salts and dibromides. A variety of phenyl and methyl vinyl sulfones have been formed in good yields, in the absence of any catalyst. Georg Thieme Verlag Stuttgart.

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.

Formation of symmetrical alkenes by homocoupling of metallated sulfones under nickel catalysis

Summary -Allylic sulfones undergo a coupling reaction with organometallic compounds (Mg or Li) not only with copper catalysts but also with iron or nickel salts. With 7,7-disubstituted allylic sulfones and also saturated aliphatic sulfones, however, another reaction was observed whereby two molecules of the starting sulfone are coupled to give symmetrical alkenes. The scope of this reaction was investigated. Elsevier.

Synthesis, structure, and stability of cyclopentadienyl(triphenylphosphine)(α-benzenesulfonylalkyl)nickel complexes

The title complexes have been prepared in moderate yields by reaction of α-sulfonyl carbanions with Cp(PPh3)NiCl; the crystal structure of two of these complexes shows that the nickel atom is linked to the α-carbon of the sulfonyl group and there is no interaction between the metal and the SO2 moiety.When their solution in benzene are warmed to 90 deg C, these complexes very cleanly yield the corresponding α,β-unsaturated sulfone (E isomer).An efficient method of dehydrogenating secondary alkyl sulfones is reported.

Organic syntheses with sulfones No. XLII. Oxidation of α-sulfonyl carbanions with cupric salts.

α-Lithiated phenylalkyl sulfones, on treatment with various cupric salts, give comparable amounts of the α,α'-dimer and the corresponding vinylic sulfone.With cupric acetate or propionate, dehydrogenation occurs selectively: primary sulfones are converted into α,β-unsaturated sulfones in high yield.

ORGANIC SYNTHESIS WITH SULFONES XXXII. A CONVENIENT ROUTE TO α,β-UNSATURATED SULFONES FROM SATURATED SULFONE

α-sulfonyl lithiated anions are oxidized by cupric carboxylates into α,β-unsaturated sulfones.Primary sulfones lead to pure trans-vinylic sulfones.