64329-88-0

Upstream product

• 591-50-4 iodobenzene 
• 28691-72-7 (E)-1-propenyl phenyl sulfone 
• 2525-42-0 phenylsulfonylpropa-1,2-diene 
• 98-80-6 phenylboronic acid 
• 3112-85-4 methylphenylsulfonate 
• 98-09-9 benzenesulfonyl chloride 
• 98-83-9 isopropenylbenzene 
• 56069-39-7 diethyl phenylsulfonylmethylphosphonate 
• 98-86-2 acetophenone 
• 704-80-3 (E)-3-phenyl-2-butenoic acid 
• 873-55-2 sodium benzenesulfonate 
• 6272-36-2 1,2-bis(benzenesulfonyl)hydrazine 
• 5670-65-5 (E)-1-nitro-2-phenyl-1-propene 
• 80-17-1 benzenesufonyl hydrazide 

Downstream Products

• 951678-65-2 (S)-((2-phenylpropyl)sulfonyl)benzene 
• 70738-48-6 phenyl 2-phenylpropyl sulfone 

Relevant academic research and scientific papers

Controllable Activation of β-Alkyl Nitroalkenes: Regioselective Synthesis of Allyl and Vinyl Sulfones

The regiospecific radical reactions of β-alkyl nitroalkenes with sulfonyl hydrazides depended to a great extent on the choice of a solvent and catalyst. In the presence of dimethylformamide (DMF), β-alkyl nitroalkenes more likely converted into electron-rich allyl nitro compounds, which reacted with sulfonyl hydrazides to afford allyl sulfones with high regioselectivity. While in acetonitrile (CH3CN), vinyl sulfones were obtained directly via sulfonation of electron-deficient β-alkyl nitroalkenes. The mechanism investigation revealed that the regioselectivity was controlled by the equilibrium of β-alkyl nitroalkenes and allyl nitro compounds.

Copper-Photocatalyzed Contra-Thermodynamic Isomerization of Polarized Alkenes

The contra-thermodynamic isomerization of α- and β-substituted cinnamate derivatives catalyzed by the Cu(OAc)2/rac-BINAP complex under blue light irradiation is reported. The use of an oxazolidinone template, which favored the complexation of the copper catalyst to the substrate, allowed the E → Z isomerization of the catalytically formed chromophore under simple and robust reaction conditions in good to excellent ratios. The mechanism of this process based on the transient formation of a chromophore was also studied.

N,N′-Disulfonylhydrazines: New sulfonylating reagents for highly efficient synthesis of (E)-vinyl sulfones at room temperature

N,N′-Disulfonylhydrazines have been proven to be the most reactive precursors of sulfonyl radicals in all types of sulfonyl substituted hydrazines as early as a half century ago. But such function has not been applied in organic synthesis except the formation of disulfones by self-dimerization of sulfonyl radicals. In this article, they were introduced as new sulfonylating reagents and their combinations with NIS and Et3N were established as excellent iodosulfonylating reagents for alkenes. Finally, a highly efficient method for the synthesis of (E)-vinyl sulfones was developed by mixing an alkene, a N,N′-disulfonylhydrazine, NIS and Et3N in THF at room temperature for 5 min.

Highly Efficient Enantioselective Synthesis of Chiral Sulfones by Rh-Catalyzed Asymmetric Hydrogenation

A highly efficient and enantioselective Rh-(R,R)-f-spiroPhos complex catalyzed hydrogenation of a series of unsaturated sulfones has been developed. With Rh-(R,R)-f-spiroPhos catalyst under mild conditions, not only the asymmetric hydrogenation of both the 3,3-diaryl and exocyclic α,β-unsaturated sulfones was first realized with up to 99.9% ee but also 3-alkyl-3-aryl and benzo[b]thiophene-1,1-dioxides were successfully hydrogenated to the corresponding chiral sulfones with excellent enantioselectivities (up to 99.4% ee) regardless of the steric hindrance, electronic property, and geometry of the substrates. Moreover, this reaction offers a route to (S)-(+)-ar-turmerone as a spice flavor, which is an important synthetic intermediate of pharmaceuticals.

Visible Light-Mediated Metal-Free Synthesis of Vinyl Sulfones from Aryl Sulfinates

Visible light and eosin Y catalyze the synthesis of vinyl sulfones from aryl sulfinates and alkenes by a photoredox process. The reaction scope is broad in aryl sulfinates and alkenes and the general and simple procedure provides a metal-free alternative for the synthesis of synthetically valuable vinyl sulfones.

PhI(OAc)2 mediated decarboxylative sulfonylation of β-aryl-α,β-unsaturated carboxylic acids: A synthesis of (E)-vinyl sulfones

A highly efficient metal-free decarboxylative sulfonylation protocol for the preparation of (E)-vinyl sulfones from of β-aryl-α,β-unsaturated carboxylic acids using sodium sulfinates and (diacetoxyiodo)benzene (PhI(OAc)2) was developed. This strategy offers a simple and expedient synthesis of (E)-vinyl sulfones bearing a wide variety of functional groups. A radical-based pathway has been proposed for this decarboxylative sulfonylation reaction.

An enantioselective approach to the preparation of chiral sulfones by ir-catalyzed asymmetric hydrogenation

Several chiral sulfonyl compounds were prepared using the iridium catalyzed asymmetric hydrogenation reaction. Vinylic, allylic and homoallylic sulfone substitutions were investigated, and high enantioselectivity is maintained regardless of the location of the olefin with respect to the sulfone. Impressive stereoselectivity was obtained for dialkyl substitutions, which typically are challenging substrates in the hydrogenation. As expected, the more bulky Z-substrates were hydrogenated slower than the corresponding E isomers, and in slightly lower enantioselectivity.

Photoredox α-vinylation of α-amino acids and N -aryl amines

A new coupling protocol has been developed that allows the union of vinyl sulfones with photoredox-generated α-amino radicals to provide allylic amines of broad diversity. Direct C-H vinylations of N-aryl tertiary amines, as well as decarboxylative vinylations of N-Boc α-amino acids, proceed in high yield and with excellent olefin geometry control. The utility of this new allyl amine forming reaction has been demonstrated via the syntheses of several natural products and a number of established pharmacophores.

Catalytic enantioselective reduction of β,β-disubstituted vinyl phenyl sulfones by using bisphosphine monoxide ligands

(Chemical Equation Presented) Synthesis of chiral sulfones: A copper-phosphine complex efficiently provided optically active alkyl phenyl sulfones by hydrosilylation at room temperature. The reduction of β,β-disubstituted vinyl sulfones in the presence of the Me-DuPhos monoxide ligand lead to excellent enantiomeric excesses and high yields (see scheme). The prepared chiral sulfones were desulfonylated and subjected to Julia olefination conditions.

Highly regio- and stereoselective palladium(0)-catalyzed addition of organoboronic acids with 1,2-allenic sulfones, sulfoxides, or alkyl- or aryl-substituted allenes in the presence of acetic acid: An efficient synthesis of E-alkenes

Two sets of reaction conditions were established to enable the palladium(0)-catalyzed addition of organoboronic acids with 1,2-allenic sulfones, sulfoxides, or alkyl- or aryl-substituted allenes in the presence of acetic acid. This reaction provides a new