Direct Transformation of Nitroalkanes to Nitriles Enabled by Visible-Light Photoredox Catalysis and a Domino Reaction Process

被引：18

作者：

Li, Yu-Hsun ^{[1
]}

Akula, Pavan Sudheer ^{[1
]}

Hong, Bor-Cherng ^{[1
]}

Peng, Chieh-Hung ^{[1
]}

Lee, Gene-Hsiang ^{[2
]}

机构：

[1] Natl Chung Cheng Univ, Dept Chem & Biochem, Chiayi 621, Taiwan

[2] Natl Taiwan Univ, Instrumentat Ctr, Taipei 106, Taiwan

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 19期

关键词：

INITIATED O-ALKYLATION; NITRO-COMPOUNDS; ELECTRON-TRANSFER; CARBOXYLIC-ACIDS; HIGHLY EFFICIENT; PRIMARY AMIDES; ALDOXIMES; CONVERSION; DEHYDRATION; OXIMES;

D O I：

10.1021/acs.orglett.9b02682

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and convenient process for direct transformation of nitroalkanes to the corresponding nitriles was developed using a visible-light photoredox catalysis strategy with household decorative blue LEDs and the additives of Et3N and DIPIBA (or DIPEA). Application of the process in secondary nitroalkanes bearing a beta-alcohol resulted in a domino process of the retro-Henry reaction and the subsequent acetalization, aldol, cyanohydrin, and ring-contraction reactions with stereoselectivities. The photocatalytic reaction was demonstrated by a continuous flow method.

引用

页码：7750 / 7754

页数：5

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