43119-53-5Relevant articles and documents
The Role of Oxygen in the Electrochemical Reduction of Ethyl 2-(2-(Bromomethyl)phenoxy)acetate at Carbon Cathodes in Dimethylformamide
Ji, Chang,Kelcher, Austin R.,Olivares, Jacob A.,Simon, Tamir,Vasquez, Antonio
, (2020/04/24)
Cyclic voltammetry (CV) and controlled-potential electrolysis (CPE) were employed to examine the direct reduction of ethyl 2-(2-(bromomethyl)phenoxy)acetate at carbon cathodes in dimethylformamide (DMF) containing tetramethylammonium tetrafluoroborate (TMABF4) as the electrolyte. Cyclic voltammogram of the substrate exhibits a single irreversible cathodic wave with a peak potential of -1.75 V vs SCE, which is characteristic for the reduction of organic halides in aprotic solvents. Bulk electrolyses of ethyl 2-(2-(bromomethyl)phenoxy)acetate were carried out in the absence and presence of oxygen. The product distributions were obtained by gas chromatograph (GC) as well as gas chromatograph coupled to a mass spectrometer (GC-MS). Two bicyclic compounds, ethyl 2,3-dihydro-1-benzofuran-2-carboxylate and ethyl benzofuran-2-carboxylate, were found to be formed in a total yield of more than 40% in the presence of oxygen. The reaction mechanism, in which the oxygen plays a significant role, was proposed and discussed on the basis of this study.
A practical synthesis of 2,3-dihydro-2-benzofurancarboxylic acid: A general route to 2,3-dihydrobenzofurans
Edwards,Readhead,Tweddle
, p. 495 - 496 (2007/10/02)
-
Palladium(II)-catalyzed asymmetric oxidative cyclization of 2-allylphenols in the presence of copper(II) acetate and molecular oxygen. Study of the catalysis of the Wacker-type oxidation
Hosokawa, Takahiro,Uno, Tetsuyuki,Inui, Shiro,Murahashi, Shun-Ichi
, p. 2318 - 2323 (2007/10/02)
The intramolecular oxidative cyclization of trans-2-(2-butenyl)phenol (2) using (+)-(3,2,10-η-pinene)palladium(II) acetate (1) in the pressure of Cu(OAc)2 and O2 has been studied in order to gain insight into the catalysis of the Wacker-type oxidation. The main results obtained are as follows: (1) the catalytically active Pd(II) species which is different from complex 1 is formed during the reaction, (2) the chiral pinanyl ligand is retained by the catalyst throughout the reaction, and (3) the catalyst consists of copper and palladium linked with an acetate bridge. These results cannot be accounted for by the conventional Wacker-type catalysis involving the reoxidation of palladium(0). A hydroperoxopalladium(II) species coupled with copper(II) acetate is most likely the active catalyst in the present reaction. A mechanism for the enantioselection is also described in comparison with the results obtained by the oxidative cyclization of cis-2-(2-butenyl)phenol.
