[Cu(OH)(TMEDA)]2Cl2‑Catalyzed Regioselective 2‑Arylation of 5‑Substituted Tetrazoles with Boronic Acids under Mild Conditions

[Cu(OH)(TMEDA)]2Cl2‑Catalyzed Regioselective 2‑Arylation of 5‑Substituted Tetrazoles with Boronic Acids under Mild Conditions

A mild and regioselective 2-arylation of 5-substituted tetrazoles is described. The reaction proceeds regio­selectively with a variety of aryl­boronic acids in the presence of [Cu(OH)(TMEDA)]2Cl2 to afford 2,5-disubstituted tetrazoles. This is the first report of highly regio­selective arylation of...

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Veröffentlicht in:Journal of organic chemistry 2014-07, Vol.79 (14), p.6703-6707
Hauptverfasser: Onaka, Takuya, Umemoto, Hideaki, Miki, Yasuyoshi, Nakamura, Akira, Maegawa, Tomohiro
Format: Artikel
Sprache:eng
Schlagworte:
Boronic Acids - chemistry
Catalysis
Coordination Complexes - chemistry
Copper - chemistry
Molecular Structure
Stereoisomerism
Tetrazoles - chemical synthesis
Tetrazoles - chemistry
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Zusammenfassung:A mild and regioselective 2-arylation of 5-substituted tetrazoles is described. The reaction proceeds regio­selectively with a variety of aryl­boronic acids in the presence of [Cu(OH)(TMEDA)]2Cl2 to afford 2,5-disubstituted tetrazoles. This is the first report of highly regio­selective arylation of 5-alkyl­tetrazoles.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo500862t