Aerobic cross-dehydrogenative couplings of N-heteroarenes with toluene derivatives at room temperature

A set of mild aerobic cross-dehydrogenative couplings of N-heteroarenes with the benzylic C(sp 3 )-H bond has been achieved by using visible-light-induced photocatalysis. This approach was found to provide a sustainable alternative to Minisci benzylation reactions using readily accessible toluene de...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2021-10, Vol.23 (19), p.779-7795
Main Authors: Wang, Qiao-Lin, Huang, Huawen, Sun, Zhaozhao, Chen, Yufeng, Deng, Guo-Jun
Format: Article
Language:English
Subjects:
Couplings
Dehydrogenation
Feasibility studies
Green chemistry
Hydrogen bonds
Light effects
Oxidation
Photocatalysis
Room temperature
Toluene
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Summary:A set of mild aerobic cross-dehydrogenative couplings of N-heteroarenes with the benzylic C(sp 3 )-H bond has been achieved by using visible-light-induced photocatalysis. This approach was found to provide a sustainable alternative to Minisci benzylation reactions using readily accessible toluene derivatives as benzylating agents. The unique combination of photocatalysis, bromo radical mediation, and aerobic oxidation proved to be the key for the success of the transformation. Mechanistic studies revealed the feasibility of both oxidative and reductive quenching of the excited photocatalyst in the initial step. The unique combination of photocatalysis, bromo radical mediation, and aerobic oxidation proved to be the key for successfully achieving the cross-dehydrogenative coupling reaction.
ISSN:1463-9262
1463-9270
DOI:10.1039/d1gc02547c