Electrochimica Acta, Vol.49, No.4, 635-640, 2004
Electrochemically induced hydrogenolysis of 1,1-dibromoalkenes to vinyl bromides
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. (C) 2003 Elsevier Ltd. All rights reserved.