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Light‐Induced Tetrazole‐Quinone 1,3‐Dipolar Cycloadditions
Author(s) -
OrtizRojano Laura,
RojasMartín Jaime,
RodríguezDiaz Ciro,
Carreño M. Carmen,
Ribagorda Maria
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904138
Subject(s) - tetrazole , cycloaddition , quinone , reagent , combinatorial chemistry , chemistry , electrochemistry , photoredox catalysis , pyrazole , photochemistry , catalysis , organic chemistry , photocatalysis , electrode
Quinones were firstly used as dipolarophiles in a photoclick 1,3‐cycloaddition with 2,5‐diaryltetrazoles, as photoactivatable predipoles, providing a novel and efficient access to three types of pyrazole‐fused quinones (indazoledione derivatives). Distinctive features of this protocol include the use of light as the unique reagent and readily available, stable, and easy to handle starting materials and good to excellent yields. Photophysical and electrochemical properties of the quinones and their potential application as photoredox catalysts are also detailed.