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Nickel‐ and Cobalt‐Catalyzed Direct Alkylation of Azoles with N ‐Tosylhydrazones Bearing Unactivated Alkyl Groups
Author(s) -
Yao Tomoyuki,
Hirano Koji,
Satoh Tetsuya,
Miura Masahiro
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201106825
Subject(s) - benzoxazole , alkylation , alkyl , cobalt , catalysis , chemistry , nickel , benzothiazole , azole , combinatorial chemistry , organic chemistry , medicinal chemistry , biology , antifungal , microbiology and biotechnology
A matter of catalyst : Azole compounds can be directly alkylated with N ‐tosylhydrazones that bear unactivated alkyl groups (see scheme; phen=1,10‐phenanthroline, Ts= p ‐toluenesulfonyl). Nickel catalysis enables the introduction of simple secondary alkyl chains into benzoxazole compounds, whereas the alkylation of 5‐aryloxazoles and benzothiazole is possible by using a cobalt catalyst.