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.
Electrochemically induced hydrogenolysis of 1,1-dibromoalkenes to vinyl bromides / Feroci, Marta; M., Orsini; L., Palombi; G., Sotgiu; Inesi, Achille. - In: ELECTROCHIMICA ACTA. - ISSN 0013-4686. - STAMPA. - 49:4(2004), pp. 635-640. [10.1016/j.electacta.2003.09.018]
Electrochemically induced hydrogenolysis of 1,1-dibromoalkenes to vinyl bromides
FEROCI, Marta;INESI, ACHILLE
2004
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 material. (C) 2003 Elsevier Ltd. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
