Highly regioselective N-2 arylation of 4,5-dibromo-1,2,3-triazole: efficient synthesis of 2-aryltriazoles.
Reaction of 4,5-dibromo-1,2,3-triazole with electron-deficient aromatic halides in the presence of potassium carbonate in DMF produces the corresponding 2-aryl-4,5-dibromotriazoles with high regioselectivity. Subsequent debromination of these triazoles by hydrogenation furnishes 2-aryltriazoles in excellent yields. Overall, this two-step process provides an efficient access to 2-aryl-1,2,3-triazoles.
Wang
Xiao-jun
XJ
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., Ridgefield, Connecticut 06877, USA. xiao-jun.wang@boehringer-ingelheim.com
Zhang
Li
L
Lee
Heewon
H
Haddad
Nizar
N
Krishnamurthy
Dhileepkumar
D
Senanayake
Chris H
CH
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006842:Hydrocarbons, Brominated; D006865:Hydrogenation; D015394:Molecular Structure; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
C545924:4,5-dibromo-1,2,3-triazole; D006842:Hydrocarbons, Brominated; D014230:Triazoles