Cathodic hydrodimerization of nitroolefins

• Michael Weßling and
• Hans J. Schäfer

Beilstein J. Org. Chem. 2015, 11, 1163–1174, doi:10.3762/bjoc.11.131

• the group of activated alkenes that can be hydrodimerized by cathodic reduction. There are many olefins with different electron withdrawing groups used for cathodic hydrodimerization, but not much is known about the behaviour of the nitro group. Synthetic applications of this group could profit from

• applied. The reaction is chemoselective as only the double bond but not the nitro group undergoes reaction, is regioselective as a ß,ß-coupling with regard to the nitro group and forms preferentially two out of six possible diastereomers as major products. Keywords: cathodic hydrodimerization; C–C bond

• reduction of the nitro group to oximes would be favoured. On the other side the electrolyte should not be aprotic as protons are required for protonation of the intermediate anions in the reductive dimerization (Scheme 1). According to the proposed mechanism for the cathodic hydrodimerization the radical