title: Brønsted acid promoted benzylic C-H bond functionalization of azaarenes: nucleophilic addition to aldehydes.
abstract: A practical Brønsted acid promoted benzylic C-H functionalization of 2-methylazaarenes and nucleophilic addition to aldehydes was developed in good to excellent yields. A six-membered hydrogen-bonding transition state is proposed to be crucial for the reaction. Ready availability of the two starting materials, the use of acetic acid as the catalyst and the facile reaction conditions will guarantee this synthetic method attractive to the synthesis of bioactive pyridine and quinoline derivatives.
authors.affiliation: Key Laboratory for Environmentally Friendly Chemistry and Application of the Ministry of Education, Department of Chemistry, Xiangtan University, Hunan, 411105, PR China.
authors.forename: Fang-Fang
authors.initials: FF
authors.lastname: Wang
authors.forename: Cui-Ping
authors.initials: CP
authors.lastname: Luo
authors.forename: Yi
authors.initials: Y
authors.lastname: Wang
authors.forename: Guojun
authors.initials: G
authors.lastname: Deng
authors.forename: Luo
authors.initials: L
authors.lastname: Yang
mesh_terms: D019342:Acetic Acid / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D001372:Aza Compounds; D011725:Pyridines; D011804:Quinolines; C037219:quinoline; C023666:pyridine; D019342:Acetic Acid