title: Copper-mediated direct alkoxylation of arenes using an N,O-bidentate directing system.
abstract: Highly effective CuCl-mediated C-H alkoxylation of arenes and heteroarenes has been developed by using a 2-aminopyridine 1-oxide moiety as an N,O-bidentate directing group. The reaction proceeds smoothly using a broad range of substrates to afford o-alkoxylated benzoic and heteroaromatic amide products. Moreover, the reaction system shows remarkable compatibility when hexafluoroisopropanol is used as a coupling parter; halogen, nitro, ether, alkoxy, ester, and sulfonyl functional groups are all tolerated. The directing group can be easily removed by base hydrolysis, affording o-alkoxylated benzoic acids.
authors.affiliation: The College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Zhengzhou University , Zhengzhou 450001, People's Republic of China.
authors.forename: Lin-Bao
authors.initials: LB
authors.lastname: Zhang
authors.forename: Xin-Qi
authors.initials: XQ
authors.lastname: Hao
authors.forename: Shou-Kun
authors.initials: SK
authors.lastname: Zhang
authors.forename: Ke
authors.initials: K
authors.lastname: Liu
authors.forename: Baozeng
authors.initials: B
authors.lastname: Ren
authors.forename: Jun-Fang
authors.initials: JF
authors.lastname: Gong
authors.forename: Jun-Long
authors.initials: JL
authors.lastname: Niu
authors.forename: Mao-Ping
authors.initials: MP
authors.lastname: Song
mesh_terms: D000631:Aminopyridines / Q000138:chemical synthesis / Q000737:chemistry*; D019817:Benzoic Acid / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003497:Cyclic N-Oxides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: C000596039:2-aminopyridine 1-oxide; D000631:Aminopyridines; D003497:Cyclic N-Oxides; D003300:Copper; D019817:Benzoic Acid