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

Literature Information

Publication Date 2023-10-24
DOI 10.1039/D3GC02701E
Impact Factor 10.182
Authors

Yu-Fang Tan, Dan Yang, Yu-Hao Yang, Jin-Feng Lv, Lan-Xi Zong, Zhi Guan, Yan-Hong He


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Abstract

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.

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