127159-20-0Relevant academic research and scientific papers
Reaction of α-methylstyrene with arylsulfonyl chlorides: Spontaneous dehydrochlorination against the Zaitsev rule
Ermolaeva, Valentina V.,Gerasimova, Nina P.,Nozhnin, Nikolai A.,Moskvichev, Yuri A.,Alov, Eugeni M.,Danilova, Angelina S.,Shutova, Irina V.,Kozlova, Olga S.
, p. 84 - 86 (2005)
The free-radical addition of arylsulfonyl chlorides to α-methylstyrene in the presence of copper chloride is accompanied by the dehydrochlorination of the adducts formed.
Allyl sulfones construction via copper catalysis from α-methylstyrene derivatives and sulfonyl chlorides
Liu, Lixia,Wang, Chengming
supporting information, (2021/12/13)
Allyl sulfones are synthesized via Cu-catalyzed ligand-free regioselective sulfonylation reaction from easily obtained α-methylstyrene derivatives and sulfonyl chlorides. This redox-neutral protocol also features a low-cost metal catalyst, broad substrate scope, good functional group tolerance and could be smoothly amplified to a gram scale. The allylic sulfone products can be used in diverse radical coupling reactions.
Photoredox/cobaloxime co-catalyzed allylation of amines and sulfonyl hydrazines with olefins to access α-allylic amines and allylic sulfones
Tong, Qing-Xiao,Xu, Hui,Zhang, Hong,Zhong, Jian-Ji
, p. 8227 - 8231 (2021/10/12)
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
Lei, Xue,Zheng, Lei,Zhang, Chuanxin,Shi, Xiaodong,Chen, Yunfeng
, p. 1772 - 1778 (2018/02/23)
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
Wang, Huei-Sin,Wu, Yan-Shin,Chang, Meng-Yang
, p. 6465 - 6470 (2017/10/10)
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.
Regiocontrolled synthesis of α-sulfonylmethyl o-nitrostyrenes via ZnI2-mediated sulfonylation and AgNO2/Pd(PPh3)4-promoted o-nitration
Chang, Meng-Yang,Chen, Han-Yu,Wang, Heui-Sin
, p. 10601 - 10610 (2018/05/31)
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.
Cascade synthesis of new aryl 2-phenylallyl sulfones from α-methylstyrene and aromatic mono- and bis-sulfonyl chlorides
Pudikova,Gerasimova,Moskvichev,Alov,Danilova,Kozlova
experimental part, p. 352 - 354 (2010/09/12)
Addition products of arenesulfonyl chlorides to α-methylstyrene in the presence of catalytic amounts of copper(II) chloride and triethylamine hydrochloride underwent fast dehydrochlorination (according to Hofmann's rule) on heating in boiling acetonitrile to give the corresponding aryl 2-phenylallyl sulfones with high selectivity. This reaction underlay a one-pot procedure for the synthesis of new compounds that attract interest as potential biologically active substances, monomers, and cross-linking agents for polymeric materials from accessible starting compounds.
