Electricity-driven 1,4-alkoxydimerization of alkenes via radical-polar crossover

In this article, an electricity-driven radical-polar crossover process for the (homo)cross-1,4-alkoxydimerization of alkenes is described. A variety of abundant and readily available (hetero)aryl alkenes and (halo)aliphatic alcohols can be used in the reaction to produce 1,4-dialkoxybutane derivatives in moderate to excellent yields. Alcohols serve as solvents and nucleophiles, participating in the reaction under mild and environmentally friendly conditions without the need for metals or oxidants. The reaction exhibits broad functional group tolerance and high product diversity. The only by-product of the reaction is hydrogen gas released at the cathode, making the method clean and highly atom-economical. The insensitivity to air enables this synthetic strategy to be efficient and convenient for the construction of various 1,4-dialkoxybutane derivatives. A gram-scale electrochemical experiment further demonstrated the synthetic utility of the method.

Automated summary

This article describes an electricity-driven radical-polar crossover process for the (homo)cross-1,4-alkoxydimerization of alkenes. A variety of abundant and readily available (hetero)aryl alkenes and (halo)aliphatic alcohols can be used in the reaction to produce 1,4-dialkoxybutane derivatives with moderate to excellent yields. The reaction exhibits broad functional group tolerance and high product diversity. The method is clean and highly atom-economical, with hydrogen gas being the only by-product. Its insensitivity to air makes it efficient and convenient for the construction of various 1,4-dialkoxybutane derivatives.