Electrochemical oxidation-induced etherification via C(sp(3))-H/O-H cross-coupling

作者:Wang, HM (Wang, Huamin)[ 1 ] ; Liang, KL (Liang, Kailun)[ 1 ] ; Xiong, WP (Xiong, Wenpeng)[ 1 ] ; Samanta, S (Samanta, Supravat)[ 1 ] ; Li, WQ (Li, Wuqin)[ 1 ] ; Lei, AW (Lei, Aiwen)[ 1,2 ]

SCIENCE ADVANCES

卷: 6 期: 20

文献号: eaaz0590

DOI: 10.1126/sciadv.aaz0590

出版年: MAY 2020

文献类型:Article

摘要

Direct electrochemical construction of C-O bonds through C(sp(3))-H functionalization still remains fundamentally challenging. Here, electrochemical oxidation-induced benzylic and allylic C(sp(3))-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(3))-H functionalization in the absence of transition metal catalysis. A series of alcohols and benzylic and allylic C(sp(3))-H compounds were compatible with this transformation. Mechanistically, the generation of aryl radical cation intermediates is the key to this C(sp(3))-H etherification, as evidenced by radical probe substrate (cyclopropane ring opening) and electron paramagnetic resonance experiments.

关键词

KeyWords Plus:ALCOHOLS; ETHERS; STRATEGIES; PHENOLS; ARYL

作者信息

通讯作者地址:

Wuhan University Wuhan Univ, Coll Chem & Mol Sci, Inst Adv Studies IAS, Wuhan 430072, Peoples R China.

Jiangxi Normal University Jiangxi Normal Univ, Natl Res Ctr Carbohydrate Synth, Nanchang 330022, Jiangxi, Peoples R China.

通讯作者地址: Lei, AW (通讯作者)

Wuhan Univ, Coll Chem & Mol Sci, Inst Adv Studies IAS, Wuhan 430072, Peoples R China.

通讯作者地址: Lei, AW (通讯作者)

Jiangxi Normal Univ, Natl Res Ctr Carbohydrate Synth, Nanchang 330022, Jiangxi, Peoples R China.

地址:

[ 1 ]‎ Wuhan Univ, Coll Chem & Mol Sci, Inst Adv Studies IAS, Wuhan 430072, Peoples R China

[ 2 ]‎ Jiangxi Normal Univ, Natl Res Ctr Carbohydrate Synth, Nanchang 330022, Jiangxi, Peoples R China

电子邮件地址:aiwenlei@whu.edu.cn