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Aryl and Heteroaryl N1‐Tetrazoles through Ligand‐Free Suzuki‐Reaction under Aerobic, Aqueous Conditions
Author(s) -
Seifried Marco,
Knoll Christian,
Giester Gerald,
Welch Jan M.,
Müller Danny,
Weinberger Peter
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700105
Subject(s) - chemistry , tetrazole , ligand (biochemistry) , aryl , combinatorial chemistry , substrate (aquarium) , aqueous medium , aqueous solution , palladium , catalysis , limiting , organic chemistry , receptor , mechanical engineering , oceanography , engineering , geology , biochemistry , alkyl
Substituted 1‐biaryl‐1 H ‐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 1 H ‐tetrazoles in very good to excellent yields is presented. The combination of PdCl 2 /NEt 3 /H 2 O/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.