Aryl and Heteroaryl N1‐Tetrazoles through Ligand‐Free Suzuki‐Reaction under Aerobic, Aqueous Conditions

Substituted 1‐biaryl‐1H‐tetrazoles are classically obtained from the corresponding 1‐aminobiaryls, limiting the selection of substrates. The development and substrate scope of a green, ligand‐free Suzuki protocol in aqueous media under ambient atmosphere, leading to 1‐biaryl‐ and heteroaryl‐substitu...

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Bibliographic Details
Published in:European journal of organic chemistry 2017-05, Vol.2017 (17), p.2416-2424
Main Authors: Seifried, Marco, Knoll, Christian, Giester, Gerald, Welch, Jan M., Müller, Danny, Weinberger, Peter
Format: Article
Language:English
Subjects:
Aqueous solutions
Cross‐coupling
C–C coupling
Green chemistry
Ligands
Palladium
Spin crossover
Substitutes
Tetrazoles
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Summary:Substituted 1‐biaryl‐1H‐tetrazoles are classically obtained from the corresponding 1‐aminobiaryls, limiting the selection of substrates. The development and substrate scope of a green, ligand‐free Suzuki protocol in aqueous media under ambient atmosphere, leading to 1‐biaryl‐ and heteroaryl‐substituted 1H‐tetrazoles in very good to excellent yields is presented. The combination of PdCl2/NEt3/H2O/EtOH was found to combine high yields and high purity for all substrates investigated. Comparative experiments investigating the reaction rate showed that the tetrazole does not act as a ligand for the palladium catalyst. The development and substrate scope of a green, ligand‐free Suzuki protocol in aqueous media under ambient atmosphere, leading to 1‐biaryl‐ and heteroaryl‐substituted 1H‐tetrazoles in very good to excellent yields is presented.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201700105