Visible-Light-Triggered Radical-Addition/Ring-Opening Cascade Reactions of 2<i>H</i>-Indazoles to Access <i>ortho</i>-Alkoxycarbonylated Azobenzenes

A series of asymmetric azobenzenes have been synthesized by radical-addition/ring-opening cascade reactions from 2<i>H</i>-indazole in the presence of PIFA and alcohols under blue light irradiation and nitrogen protection. Furthermore, a wide range of functional groups were tolerated and the corresponding products were obtained in 30% to 95% isolated yields. The protocol is characterized by its visible-light initiation, avoidance of metals and photocatalysts, mild reaction conditions, and may find potential use in materials science and medicinal chemistry.

Authors

Institutions

Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-10-08
DOI
https://doi.org/10.1021/acs.joc.4c01475
Primary Topic
Photochromic and Fluorescence Chemistry
Type
article
Field-Weighted Citation Impact
0.00

Funders

Controls
|||
ALL TIME
JAN
FEB
MAR
APR
MAY
JUN
JUL
AUG
SEP
OCT
article

Visible-Light-Triggered Radical-Addition/Ring-Opening Cascade Reactions of 2H-Indazoles to Access ortho-Alkoxycarbonylated Azobenzenes

Dayou Rong, Yuanyuan Xie, Fenghao Dai, Yingyan Cao et al.
The Journal of Organic Chemistry
Photochromic and Fluorescence Chemistry
article

Visible-Light-Triggered Radical-Addition/Ring-Opening Cascade Reactions of 2H-Indazoles to Access ortho-Alkoxycarbonylated Azobenzenes

Dayou Rong, Yuanyuan Xie, Fenghao Dai, Yingyan Cao, Zhenhua Li, Lijun Chen, Longfeng Yuan, Zhihong Zhao
article en

Abstract

A series of asymmetric azobenzenes have been synthesized by radical-addition/ring-opening cascade reactions from 2<i>H</i>-indazole in the presence of PIFA and alcohols under blue light irradiation and nitrogen protection. Furthermore, a wide range of functional groups were tolerated and the corresponding products were obtained in 30% to 95% isolated yields. The protocol is characterized by its visible-light initiation, avoidance of metals and photocatalysts, mild reaction conditions, and may find potential use in materials science and medicinal chemistry.

The Journal of Organic ChemistryVol. 89(20)
Zhejiang University of Technology (CN)
Basic Public Welfare Research Program of Zhejiang Province
Openalex Percentile: Top 89%
Photochromic and Fluorescence Chemistry
AI Navigator

Ask Laika to Summarize, Analyze, and Connect papers live on the map.

Summarize Papers & Methodologies

Extract key findings, datasets, and comparative methods across publications.

Benchmark Rankings & Visual Analytics

Rank top research institutions, authors, funders, topics, and journals by Field-Weighted Citation Impact (FWCI) and paper volume with instant charts.

Connect Distant Disciplines

Bridge topological clusters on the map to find hidden collaborative intersections.