Affiliation:
1. State Key Laboratory and Institute of Elemento-Organic Chemistry Frontiers Science Center for New Organic Matter College of Chemistry Nankai University 94 Weijin Road Tianjin 300071 China
2. State Key Laboratory of Coordination Chemistry School of Chemistry and Chemical Engineering Nanjing University Nanjing 210023 P. R. China
Abstract
AbstractHerein, an electrochemically driven NiH‐catalyzed reductive coupling of alkyl halides and alkyl alkenes for the construction of Csp3−Csp3bonds is firstly reported. Notably, alkyl halides serve dual function as coupling substrates and as hydrogen sources to generate NiH species under electrochemical conditions. The tunable nature of this reaction is realized by introducing an intramolecular coordinating group to the substrate, where the product can be easily adjusted to give the desired branched products. The method proceeds under mild conditions, exhibits a broad substrate scope, and affords moderate to excellent yields with over 70 examples, including late‐stage modification of natural products and drug derivatives. Mechanistic insights offer evidence for an electrochemically driven coupling process. Thesp3‐carbon‐halogen bonds can be activated through single electron transfer (SET) by the nickel catalyst in its low valence state, generated by cathodic reduction, and the generation of NiH species from alkyl halides is pivotal to this transformation.
Funder
National Key Research and Development Program of China
National Natural Science Foundation of China