Green oxidation of indoles using halide catalysis

被引：117

作者：

Xu, Jun ^{[1
,2
,3
]}

Liang, Lixin ^{[2
]}

Zheng, Haohao ^{[1
]}

Chi, Yonggui Robin ^{[3
]}

Tong, Rongbiao ^{[2
]}

机构：

[1] Guizhou Univ Tradit Chinese Med, Coll Pharm, Guiyang, Guizhou, Peoples R China

[2] HKUST, Dept Chem, Kowloon, Clear Water Bay, Hong Kong, Peoples R China

[3] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

NATURE COMMUNICATIONS | 2019年 / 10卷 / 1期

基金：

中国国家自然科学基金;

关键词：

C-H; ALKALOIDS; OXINDOLE; REARRANGEMENT; CONVERSION; ROUTE; TRANSFORMATIONS; MITRAPHYLLINE; PHYSOSTIGMINE; DERIVATIVES;

D O I：

10.1038/s41467-019-12768-4

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Oxidation of indoles is a fundamental organic transformation to deliver a variety of synthetically and pharmaceutically valuable nitrogen-containing compounds. Prior methods require the use of either organic oxidants (meta-chloroperoxybenzoic acid, N-bromosuccinimide, t-BuOCl) or stoichiometric toxic transition metals [Pb(OAc)(4), OsO4, CrO3], which produced oxidant-derived by-products that are harmful to human health, pollute the environment and entail immediate purification. A general catalysis protocol using safer oxidants (H2O2, oxone, O-2) is highly desirable. Herein, we report a unified, efficient halide catalysis for three oxidation reactions of indoles using oxone as the terminal oxidant, namely oxidative rearrangement of tetrahydro-beta-carbolines, indole oxidation to 2-oxindoles, and Witkop oxidation. This halide catalysis protocol represents a general, green oxidation method and is expected to be used widely due to several advantageous aspects including waste prevention, less hazardous chemical synthesis, and sustainable halide catalysis.

引用

页数：11

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