title: Copper-Catalyzed Oxidative C(sp(3))-H Functionalization for Facile Synthesis of 1,2,4-Triazoles and 1,3,5-Triazines from Amidines.
abstract: A facile and versatile catalytic system involving copper catalyst, K3PO4 as the base, and O2 as the oxidant has been developed to enable efficient synthesis of 2,4,6-trisubstituted and 2,6-disubstituted 1,3,5-triazines and 1,3-disubstituted 1,2,4-triazoles from amidines with trialkylamines, DMSO, and DMF as the reaction partners, respectively. This protocol features inexpensive metal catalyst, green oxidant, good functional group tolerance, and high regioselectivity, providing an efficient entry to those products that are challenging to prepare by traditional methods. A single-electron-transfer (SET) mechanism is proposed for these transformations.
authors.affiliation: †School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China.
authors.forename: Huawen
authors.initials: H
authors.lastname: Huang
authors.affiliation: †School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China.|‡Key Laboratory of Organo-pharmaceutical Chemistry of Jiangxi Province, Gannan Normal University, Ganzhou 341000, P. R. China.
authors.forename: Wei
authors.initials: W
authors.lastname: Guo
authors.affiliation: †School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China.
authors.forename: Wanqing
authors.initials: W
authors.lastname: Wu
authors.affiliation: §Department of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University 801 Sherbrooke Street W, Montreal, Quebec H3A 0B8, Canada.
authors.forename: Chao-Jun
authors.initials: CJ
authors.lastname: Li
authors.affiliation: †School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China.
authors.forename: Huanfeng
authors.initials: H
authors.lastname: Jiang
mesh_terms: D000578:Amidines / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D014227:Triazines / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000578:Amidines; D009942:Organometallic Compounds; D014227:Triazines; D014230:Triazoles; C045575:1,2,4-triazole; D003300:Copper