Preparation of 2‑(2H‑Tetrazol-2-yl)benzoic Acids via Regioselective Cu(I) Catalyzed N2 Arylation of Tetrazole

2-(2H-Tetrazol-2-yl)­benzoic acid 1 and analogs were prepared via Cu­(I) catalyzed C–N coupling of 2-iodo or 2-bromo benzoic acids with 5-(ethylthio)-1H-tetrazole followed by reductive cleavage of the thioether bond. The C–N coupling was regioselective toward the N2-position on tetrazole. The scope...

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Published inOrganic process research & development Vol. 23; no. 11; pp. 2354 - 2361
Main Authors Song, Zhiguo Jake, Maligres, Peter, Molinaro, Carmela, Humphrey, Guy, Fritzen, Jeff, Wilson, Jonathan, Chen, Yonggang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.11.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Applied
Chemistry, Organic
Physical Sciences
Science & Technology
Tetrazole benzoic acid
N-2 regioselective tetrazole arylation
MEDICINAL CHEMISTRY
5-SUBSTITUTED TETRAZOLES
2,5-DISUBSTITUTED TETRAZOLES
SALTS
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Summary:2-(2H-Tetrazol-2-yl)­benzoic acid 1 and analogs were prepared via Cu­(I) catalyzed C–N coupling of 2-iodo or 2-bromo benzoic acids with 5-(ethylthio)-1H-tetrazole followed by reductive cleavage of the thioether bond. The C–N coupling was regioselective toward the N2-position on tetrazole. The scope of this methodology was demonstrated on a series of 2-halobenzoic acid substrates in moderate yields.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.9b00243