16619-56-0Relevant articles and documents
The Electrochemical cis-Chlorination of Alkenes
Strehl, Julia,Fastie, Cornelius,Hilt, Gerhard
supporting information, p. 17341 - 17345 (2021/10/23)
The first example for the electrochemical cis-dichlorination of alkenes is presented. The reaction can be performed with little experimental effort by using phenylselenyl chloride as catalyst and tetrabutylammoniumchloride as supporting electrolyte, which also acts as nucleophilic reagent for the SN2-type replacement of selenium versus chloride. Cyclic voltammetric measurements and control experiments revealed a dual role of phenylselenyl chloride in the reaction. Based on these results a reaction mechanism was postulated, where the key step of the process is the activation of a phenylselenyl chloride-alkene adduct by electrochemically generated phenylselenyl trichloride. Like this, different aliphatic and aromatic cyclic and acyclic alkenes were converted to the dichlorinated products. Thereby, throughout high diastereoselectivities were achieved for the cis-chlorinated compounds of >95 : 5 or higher.
Preparation method of dichloro addition product of aromatic olefin under visible light catalysis
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Paragraph 0078-0081, (2020/06/30)
The invention relates to a preparation method of a dichloro addition product of aromatic olefin under visible light catalysis. The preparation method comprises the following step: by taking aromatic olefin as a substrate and copper chloride with visible light absorption capability as a chlorine source, reacting in an organic solvent under the irradiation of visible light in an inert atmosphere toobtain a dichloro addition product of the aromatic olefin after the reaction is completed. The aromatic olefin comprises a carbon-carbon double bond and an aryl group connected with the carbon-carbondouble bond through a covalent bond. Visible light is used for providing energy required by the reaction, copper chloride with visible light absorption capacity and a reaction substrate are used for photoinduction of chlorine atom transfer and initiation of an addition reaction to obtain a dichloro addition product, and the method is mild in reaction condition, simple and convenient to operate andwide in universality of the reaction substrate.
Simple and practical halogenation of arenes, alkenes and alkynes with hydrohalic acid/H2O2 or TBHP)
Barhate, Nivrutti B.,Gajare, Anil S.,Wakharkar, Radhika D.,Bedekar, Ashutosh V.
, p. 11127 - 11142 (2007/10/03)
A simple protocol for the halogenation of arenes utilizing a combination of aqueous hydrogen peroxide (34 %) or tert-butylhydroperoxide (70 %) and hydrohalic acid is presented. A similar procure of oxyhalogenation involving the in situ generation of positive halogen reagents is applied for the preparation of vicinal trans-dibromoalkanes and dichloroalkanes from alkenes. The reaction of alkenes with a combination of hydrochloric acid and hydrobromic acid with hydrogen peroxide gave a mixture of 1-bromo 2-chloro alkanes and 1,2-dibromoalkanes: Oxidative bromination of alkynes is also reported under similar conditions.
