82665-92-7Relevant academic research and scientific papers
Efficient Electrocatalysis for the Preparation of (Hetero)aryl Chlorides and Vinyl Chloride with 1,2-Dichloroethane
Liang, Yujie,Lin, Fengguirong,Adeli, Yeerlan,Jin, Rui,Jiao, Ning
supporting information, p. 4566 - 4570 (2019/02/14)
Although the application of 1,2-dichloroethane (DCE) as a chlorinating reagent in organic synthesis with the concomitant release of vinyl chloride as a useful byproduct is a fantastic idea, it still presents a tremendous challenge and has not yet been achieved because of the harsh dehydrochlorination conditions and the sluggish C?H chlorination process. Here we report a bifunctional electrocatalysis strategy for the catalytic dehydrochlorination of DCE at the cathode simultaneously with anodic oxidative aromatic chlorination using the released HCl as the chloride source for the efficient synthesis of value-added (hetero)aryl chlorides. The mildness and practicality of the protocol was further demonstrated by the efficient late-stage chlorination of bioactive molecules.
Electron Transfer Reactions. A Reinvestigation of the Chlorination of 1-Methyl-2-phenylindole with N-Chlorobenzotriazole. The Role of Oxygen and Oxygenated Solvent
Carloni, Patricia,Eberson, Lennart,Greci, Lucedio,Stipa, Pierluigi,Tosi, Giorgio
, p. 1779 - 1784 (2007/10/02)
1-Methyl-2-phenylindole (1, MPI-H) reacts with N-chlorobenztriazole (2, BT-Cl) to form the corresponding radical cation (MPI-H).+ which itself, or via the indolyl radical (MPI).+, formed by deprotonation of MPI-H.+, reacts with oxygen or a nucleophilic solvent leading to indoxyls 4-7.Cyclic voltammetric studies, as well as the oxidation of MPI-H with BT-Cl carried out in the EPR cavity, show that the radical cation MPI-H.+ dimerizes to give 3,3'-(MPI)2 8 which is transformed into the corresponding radical cation 3,3'-(MPI)2.+ in the reaction medium.The identi ty of this radical cation has been confirmed by oxidizing 3,3'-(MPI)2 directly.The formation of the radical cations MPI-H.+ and 3,3'-(MPI)2.+ has been monitored by UV-VIS spectroscopy and their decay rate constants measured.
New Aspects in the Chlorination of Indoles with 1-Chlorobenzotriazole and 1-Chloroisatin
Berti, C.,Greci, L.,Andruzzi, R.,Trazza, A.
, p. 4895 - 4899 (2007/10/02)
2-Phenyl-, 1-methyl-2-phenyl-, and 2-phenyl-3-methylindole react with 1-chlorobenzotriazole and 1-chloroisatin to form essentially 3-chloroindoles.The composition of the products, which depends on the solvent used, suggests an electron-transfer process fo
