Vinyl bromides 2a-f, useful intermediates in organic synthesis, have been obtained under mild conditions and in good yields via electrochemical reduction of 1,1-dibromoalkenes 1a-f (readily available substrates). The reduction has been carried out in MeCN-tetraethylammonium perchlorate (TEAP) solutions, in the presence of a proton donor, at a Au, Hg, C or Ag cathode. The use of specific reducing agents, catalysts and bases, employed in the classical procedures, has been avoided. The isomeric E/Z ratio in vinyl bromides 2a-f is affected by the cathode material
Feroci, M., Orsini, M., Sotgiu, G., Inesi, A. (2004). Electrochemically induced hydrogenolysis of 1,1-dibromoalkenes to vinyl bromides. ELECTROCHIMICA ACTA, 4, 635-640.
Electrochemically induced hydrogenolysis of 1,1-dibromoalkenes to vinyl bromides
ORSINI, MONICA;SOTGIU, Giovanni;
2004-01-01
Abstract
Vinyl bromides 2a-f, useful intermediates in organic synthesis, have been obtained under mild conditions and in good yields via electrochemical reduction of 1,1-dibromoalkenes 1a-f (readily available substrates). The reduction has been carried out in MeCN-tetraethylammonium perchlorate (TEAP) solutions, in the presence of a proton donor, at a Au, Hg, C or Ag cathode. The use of specific reducing agents, catalysts and bases, employed in the classical procedures, has been avoided. The isomeric E/Z ratio in vinyl bromides 2a-f is affected by the cathode materialI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
