Tertiary-Alcohol-Directed Functionalization of Remote C(sp3)-H Bonds by Sequential Hydrogen Atom and Heteroaryl Migrations

被引：184

作者：

Wu, Xinxin ^{[1
]}

Wang, Mingyang ^{[1
]}

Huan, Leitao ^{[1
]}

Wang, Dongping ^{[1
]}

Wang, Jinwei ^{[1
]}

Zhu, Chen ^{[1
]}

机构：

[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, 199 Ren Ai Rd, Suzhou 215123, Jiangsu, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 06期

基金：

中国国家自然科学基金;

关键词：

C-H activation; electron transfer; heteroaryls; photocatalysis; radicals; VISIBLE-LIGHT PHOTOCATALYSIS; COUPLED ELECTRON-TRANSFER; PHOTOREDOX CATALYSIS; ALKOXY RADICALS; PHOTOCHEMICAL-REACTION; H BONDS; GENERATION; CLEAVAGE; TETRAHYDROFURANS; HYPOCHLORITES;

D O I：

10.1002/anie.201709025

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reported for the first time is a tertiary-alcohol-guided heteroarylation of remote C(sp(3))-H bonds. The mild and direct generation of alkoxyl radicals from alcohols is enabled by visible-light photocatalysis. A remote hydrogen atom and heteroaryl migration sequence are involved in the reaction. Many sensitive groups remain intact in the reaction, thus illustrating wide functional-group compatibility. This protocol provides a practical strategy for the late-stage modification of alkyl ketones.

引用

页码：1640 / 1644

页数：5

共 70 条

[1]

[Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1002/ANIE.201201666

[2]

[Anonymous], 2011, Angew. Chem

[3] Mechanistic aspects of β-bond-cleavage reactions of aromatic radical cations [J].