American Chemical Society
ol5b02021_si_001.pdf (1.76 MB)

Negishi Approach to 1,5-Disubstituted 3‑Amino‑1H‑1,2,4-triazoles

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journal contribution
posted on 2015-10-02, 00:00 authored by Jeff Shen, Brian Wong, Chunang Gu, Haiming Zhang
An efficient synthesis of 1,5-disubstituted 3-amino-1H-1,2,4-triazoles has been achieved via a Negishi coupling of aryl or vinyl bromides and 1-substituted 3-amino-1H-1,2,4-triazoles in the presence of Knochel’s base tetramethylpiperidinylzinc chloride lithium chloride (TMPZnCl·LiCl) and catalytic bis­(di-tert-butylphenylphosphine)palladium chloride. This chemistry tolerates a variety of electronically diverse aryl or vinyl bromides and 1-substituted 3-amino-1H-1,2,4-triazoles.