Stereochemical study on electrochemical carboxylation of vinyl triflates

A stereochemical study on electrochemical carboxylation of ethoxycarbonyl- or phenyl-substituted vinyl triflates was carried out. Vinyl triflates in D MF with a platinum cathode and a magnesium anode underwent electrochemical carboxylation with retention of their geometries to give the corresponding alpha,beta -unsaturated carboxylic acids in moderate to good yields. The st ereochemical outcome of these electrochemical carboxylations is discussed b y comparison with predominant formation of a (Z)-isomer from either (E)- or (Z)-vinyl bromides. (C) 2001 Elsevier Science B.V. All rights reserved.