127159-25-5

Upstream product

• 3360-54-1 3-bromo-2-phenylprop-1-ene 
• 34176-08-4 sodium 4-bromobenzenesulfinate 
• 98-83-9 isopropenylbenzene 
• 98-86-2 acetophenone 
• 98-58-8 4-bromobenzenesulfonyl chloride 
• 5670-65-5 (E)-1-nitro-2-phenyl-1-propene 
• 1195-33-1 4-bromo-benzenesulfinic acid 
• 2297-64-5 p-bromophenylsulfonyl hydrazide 

Relevant academic research and scientific papers

Regiocontrolled synthesis of α-sulfonylmethyl o-nitrostyrenes via ZnI2-mediated sulfonylation and AgNO2/Pd(PPh3)4-promoted o-nitration

We report herein the AgNO2/Pd(PPh3)4-promoted regiocontrolled o-nitration of α-sulfonylmethylstyrenes in MeNO2 with good yields. The o-nitration process provides a series of sulfonyl o-nitrostyrenes. Substituted α-sulfonylmethylstyrenes were synthesized from ZnI2-mediated sulfonylation of substituted α-methylstyrenes and sodium sulfinates (RSO2Na) in MeCN with good to excellent yields. The structures of the key products were confirmed by X-ray crystallography. A plausible mechanism has been proposed herein.

Photoredox/cobaloxime co-catalyzed allylation of amines and sulfonyl hydrazines with olefins to access α-allylic amines and allylic sulfones

Herein, we reported a dual-catalytic platform for the allylation of amines and sulfonyl hydrazines with olefins to selectively access α-allylic amines and allylic sulfones in good yields by combining photoredox catalysis and cobaloxime catalysis. This strategy avoided the use of a stoichiometric amount of terminal oxidant and the use of pre-functionalized allylic precursors, representing a green and ideal atom- & step-economical process. Good substrate scope and gram-scale synthesis demonstrated the utility of this protocol. Mechanistic studies revealed that a radical process is probably involved in this reaction.

Allylic C-S Bond Construction through Metal-Free Direct Nitroalkene Sulfonation

A metal-free, open-flask protocol was developed for the preparation of allylic sulfones through direct condensation of sodium arylsulfinates and β,β-disubstituted nitroalkenes. The key step of this process was the Lewis base-promoted equilibrium between nitroalkenes and allylic nitro compounds. Through this process, the readily available conjugated nitroalkenes can be easily converted into allylic nitro compounds, which contain more reactive C=C bonds toward the sulfonyl radical addition. As a result, allylic sulfones were prepared in excellent yields with a broad substrate scope under mild conditions.

Sulfonylative alkoxyhydroxylation of 2-arylpropenes

One-pot three-step sulfonylative alkoxyhydroxylation of 2-arylpropenes 1 affords oxygenated sulfonylcumenes 4 in moderate yields via a sequential route: (i) NBS-mediated allylic bromination of 2-arylpropenes 1 in CH2Cl2, (ii) sodium sulfinates 2-promoted nucleophilic substitution of the resulting styryl bromides in a co-solvent of alcohol and water, and (iii) V2O5/H2O2 mediated alkoxyhydroxylation of corresponding styryl sulfones 3 in alcohol. The synthetic route provides a highly effective protocol for the 1,2,3-tricarbofunctionalization of 2-arylpropenes 1 via two carbon-oxygen and one carbon-sulfur bond formations.

Visible-light induced oxidant-free oxidative cross-coupling for constructing allylic sulfones from olefins and sulfinic acids

An oxidant-free dehydrogenative sulfonylation of α-methyl-styrene derivatives was developed for the construction of allylic sulfones by using eosin Y as a photosensitizer in conjunction with a cobaloxime catalyst. The process features a low-cost metal catalyst and atom economy, which provides an appealing strategy for future synthetic chemistry.

Tetrabutylammonium iodide catalyzed allylic sulfonylation of α-methyl styrene derivatives with sulfonylhydrazides

Sulfonyl radicals generated from sulfonylhydrazides by the Bu 4NI-tert-butyl hydroperoxide (TBHP) catalysis system underwent addition to a variety of α-methyl styrene derivatives to give the corresponding allylic sulfones. This selective allylic sulfonylation is metal-free, operationally simple, and environmentally friendly. The Royal Society of Chemistry 2012..