Organic Process Research & Development
Organic Process Research & Development
5 years ago

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

[ASAP] Preparation of 2-(2H-Tetrazol-2-yl)benzoic Acids via Regioselective Cu(I) Catalyzed N2 Arylation of Tetrazole
Zhiguo Jake Song, Peter E. Maligres, Carmela Molinaro, Guy R. Humphrey, Jeff Fritzen, Jonathan Wilson, Yonggang Chen
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.

Publisher URL: http://feedproxy.google.com/~r/acs/oprdfk/~3/CKeDBZIpgzI/acs.oprd.9b00243

DOI: 10.1021/acs.oprd.9b00243

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