Electrochemical Oxidative Carbon-Atom Difunctionalization: Towards Multisubstituted Imino Sulfide Ethers

作者:Guan, ZP (Guan, Zhipeng)[ 1,2 ] ; Zhu, SX (Zhu, Shuxiang)[ 1,2 ] ; Wang, SY (Wang, Siyuan)[ 1,2 ] ; Wang, HM (Wang, Huamin)[ 1,2 ] ; Wang, SY (Wang, Siyuan)[ 1,2 ] ; Zhong, XX (Zhong, Xingxing)[ 1,2 ] ; Bu, FX (Bu, Faxiang)[ 1,2 ] ; Cong, HJ (Cong, Hengjiang)[ 1,2 ] ; Lei, AW (Lei, Aiwen)[ 1,2 ]

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

DOI: 10.1002/anie.202011329

Early access icon在线发表日期: NOV 2020

文献类型:Article; Early Access

摘要

Ethers (C-O/S) are ubiquitously found in a wide array of functional molecules and natural products. Nonetheless, the synthesis of imino sulfide ethers, containing an N(sp(2))=C(sp(2))-O/S fragment, still remains a challenge because of its sensitivity to acid. Developed here in is an unprecedented electrochemical oxidative carbon-atom difunctionalization of isocyanides, providing a series of novel multisubstituted imino sulfide ethers. Under metal-free and external oxidant-free conditions, isocyanides react smoothly with simple and readily available mercaptans and alcohols. Importantly, the procedure exhibited high stereoselectivities, excellent functional-group tolerance, and good efficiency on large-scale synthesis, as well as further derivatization of the products.

关键词

作者关键词:electrochemistry; ethers; isocyanides; radicals; synthetic methods

KeyWords Plus:OLEFIN COUPLING REACTIONS; C-O; ALKENES; FUNCTIONALIZATION; AZOLES

作者信息

通讯作者地址:

Wuhan University Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China.

Wuhan University Wuhan Univ, Inst Adv Studies, Wuhan 430072, Hubei, Peoples R China.

通讯作者地址: Lei, AW (通讯作者)

Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China.

通讯作者地址: Lei, AW (通讯作者)

Wuhan Univ, Inst Adv Studies, Wuhan 430072, Hubei, Peoples R China.

地址:

[ 1 ]‎ Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China

[ 2 ]‎ Wuhan Univ, Inst Adv Studies, Wuhan 430072, Hubei, Peoples R China

电子邮件地址:aiwenlei@whu.edu.cn