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

• Published in: Green chemistry : an international journal and green chemistry resource : GC 2023-11, Vol.25 (22), p.9388-9393
• Main Authors: Tan, Yu-Fang, Yang, Dan, Yang, Yu-Hao, Lv, Jin-Feng, Zong, Lan-Xi, Guan, Zhi, He, Yan-Hong
• Format: Article
• Language: English
• Subjects: Alcohols; Aliphatic alcohols; Alkenes; Cathodic cleaning; Crossovers; Electricity; Electrochemistry; Functional groups; Green chemistry; Metals; Nucleophiles; Oxidants; Oxidizing agents
• ISSN: 1463-9262; 1463-9270
• DOI: 10.1039/D3GC02701E

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.