title: Cu(OTf)2-catalyzed selective arene C-H bond hydroxylation and nitration with KNO2 as an ambident O- and N-nucleophile via a Cu(II)-Cu(III)-Cu(I) mechanism.
abstract: Cu(OTf)2-catalyzed selective arene C-H bond hydroxylation and nitration reactions of azacalix[1]arene[3]pyridines were achieved using KNO2 as an ambident O- and N-nucleophile under very mild aerobic conditions to yield functionalized azacalixaromatics. The reaction, which selectivity between hydroxylation and nitration was modulated by the reaction medium employed, proceeded through a Cu(II)-Cu(III)-Cu(I) mechanism.
authors.affiliation: Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
authors.forename: Hu
authors.initials: H
authors.lastname: Zhang
authors.forename: Liang
authors.initials: L
authors.lastname: Zhao
authors.forename: De-Xian
authors.initials: DX
authors.lastname: Wang
authors.forename: Mei-Xiang
authors.initials: MX
authors.lastname: Wang
mesh_terms: D047250:Calixarenes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006900:Hydroxylation; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D009573:Nitrites / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*
chemical_list: D008698:Mesylates; D009573:Nitrites; D011725:Pyridines; D047250:Calixarenes; D003300:Copper; C041349:potassium nitrite; C012077:trifluoromethanesulfonic acid