Reductive Arylation of Aliphatic and Aromatic Aldehydes with Cyanoarenes by Electrolysis for the Synthesis of Alcohols

• DOI: 10.1021/acs.orglett.1c00920
• Publication Date: 2021-04-16T15:29:48Z
• Authors: Xiao Zhang; Chao Yang; Han Gao; Lei Wang; Lin Guo; Wujiong Xia
• Keywords: 01 natural sciences; 0104 chemical sciences

An electroreductive arylation reaction of aliphatic and aromatic aldehydes as well ketones with electro-deficient (hetero)arenes is described. A variety cyano(hetero)arenes carbonyl compounds, especially aldehydes, have been examined, providing secondary tertiary alcohols in moderate to good yields. Mechanistic studies, including cyclic voltammetry (CV), electron paramagnetic resonance (EPR), divided-cell experiments, support the generation ketyl radicals persistent heteroaryl radical anions via cathodic reduction followed by radical-radical cross-coupling.