Issue 15, 2021

Controllable chemoselectivity in the reaction of 2H-indazoles with alcohols under visible-light irradiation: synthesis of C3-alkoxylated 2H-indazoles and ortho-alkoxycarbonylated azobenzenes

Abstract

A high chemoselectivity in the visible-light-induced reaction of 2H-indazoles with alcohols controlled by the reaction atmosphere (N2 or O2) was achieved. Under a N2 atmosphere, an alkoxylation of 2H-indazoles with alcohols in the presence of Mes-Acr+ClO4 as a photosensitizer and Selectfluor as an oxidant generated C3-alkoxylated 2H-indazoles in high yields. Under an O2 atmosphere in the absence of Selectfluor, the reaction underwent a ring opening of 2H-indazoles to afford unsymmetrical ortho-alkoxycarbonylated azobenzenes in good yields.

Graphical abstract: Controllable chemoselectivity in the reaction of 2H-indazoles with alcohols under visible-light irradiation: synthesis of C3-alkoxylated 2H-indazoles and ortho-alkoxycarbonylated azobenzenes

Supplementary files

Article information

Article type
Research Article
Submitted
16 Apr 2021
Accepted
06 Jun 2021
First published
07 Jun 2021

Org. Chem. Front., 2021,8, 4230-4236

Controllable chemoselectivity in the reaction of 2H-indazoles with alcohols under visible-light irradiation: synthesis of C3-alkoxylated 2H-indazoles and ortho-alkoxycarbonylated azobenzenes

M. Sun, L. Li, L. Wang, J. Huo, M. Sun and P. Li, Org. Chem. Front., 2021, 8, 4230 DOI: 10.1039/D1QO00592H

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