Electrochemical oxidation-induced etherification via C(sp3)─H/O─H cross-coupling
Huamin Wang1, Kailun Liang1, Wenpeng Xiong1
1Institute for Advanced Studies (IAS), College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, P. R. China.
Abstract:
Direct electrochemical construction of C─O bonds through C(sp3)─H functionalization still remains fundamentally challenging. Here, electrochemical oxidation-induced benzylic and allylic C(sp3)─H etherification has been developed. This protocol not only offers a practical strategy for the construction of C─O bonds using nonsolvent amounts of alcohols but also allows direct electrochemical benzylic and allylic C(sp3)─H functionalization in the absence of transition metal catalysis. A series of alcohols and benzylic and allylic C(sp3)─H compounds were compatible with this transformation. Mechanistically, the generation of aryl radical cation intermediates is the key to this C(sp3)─H etherification, as evidenced by radical probe substrate (cyclopropane ring opening) and electron paramagnetic resonance experiments.
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