title: C-H bonds as ubiquitous functionality: preparation of multiple regioisomers of arylated 1,2,4-triazoles via C-H arylation.
abstract: We describe a general approach for the synthesis of complex aryl 1,2,4-triazoles. The electronic character of the C-H bonds and the triazole ring allows for the regioselective C-H arylation of 1-alkyl- and 4-alkyltriazoles under catalytic conditions. We have also developed the SEM and THP switch as well as trans-N-alkylation, which enable sequential arylation of the triazole ring to prepare 3,5-diaryltriazoles. This new strategy provides rapid access to a variety of arylated 1,2,4-triazoles and well complements existing cyclization methods.
authors.affiliation: Department of Chemistry, Columbia University, 3000 Broadway, New York, New York, 10027, USA.
authors.forename: Jung Min
authors.initials: JM
authors.lastname: Joo
authors.forename: Pengfei
authors.initials: P
authors.lastname: Guo
authors.forename: Dalibor
authors.initials: D
authors.lastname: Sames
mesh_terms: D000478:Alkylation; D002384:Catalysis; D003500:Cyclization; D006860:Hydrogen Bonding; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D014230:Triazoles; D010165:Palladium