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Electrochemical oxidation-induced etherification via C(sp3)?H/O?H cross-coupling.


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.

SUBMITTER: Wang H 

PROVIDER: S-EPMC7228760 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Electrochemical oxidation-induced etherification via C(sp<sup>3</sup>)─H/O─H cross-coupling.

Wang Huamin H   Liang Kailun K   Xiong Wenpeng W   Samanta Supravat S   Li Wuqin W   Lei Aiwen A  

Science advances 20200515 20


Direct electrochemical construction of C─O bonds through C(sp<sup>3</sup>)─H functionalization still remains fundamentally challenging. Here, electrochemical oxidation-induced benzylic and allylic C(sp<sup>3</sup>)─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(sp<sup>3</sup>)─H functionalization in the absence of transition  ...[more]

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