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Pyrene‐Tagged Chloro Oximes as Ambient‐Light‐Accelerated Ligation Agents
Author(s) -
Offenloch Janin T.,
Bastian Simon,
Mutlu Hatice,
BarnerKowollik Christopher
Publication year - 2019
Publication title -
chemphotochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.13
H-Index - 18
ISSN - 2367-0932
DOI - 10.1002/cptc.201800211
Subject(s) - cycloaddition , nitrile , pyrene , chromophore , photochemistry , oxime , chemistry , oxide , combinatorial chemistry , visible spectrum , materials science , catalysis , organic chemistry , optoelectronics
We demonstrate how a normally base‐induced or transition‐metal‐catalyzed cycloaddition reaction can be executed without additives by equipping the reactant with a chromophore as a light‐harvesting unit, able to exploit light to boost the reaction. Specifically, we generate a highly reactive nitrile oxide upon light irradiation which is able to undergo cycloaddition reactions with a wide range of substrates by introducing a pyrene unit into the oxime precursor. Commercially available LED setups, and even ambient light, were successfully employed to induce the cycloaddition. Our approach demonstrates that the careful design of light‐harvesting chromophores can be a powerful tool to facilitate light‐induced chemical transformations.