title: Dual Behavior of Iodine Species in Condensation of Anilines and Vinyl Ethers Affording 2-Methylquinolines.
abstract: A metal-free, mild and efficient method for the synthesis of 2-methylquinolines was successfully developed by condensation of anilines with vinyl ethers in the presence of catalytic amount of iodine. Modification of both pyridine and benzene moieties was easily achieved by changing only the vinyl ether and aniline. In this reaction, the iodine species was revealed to show dual behavior; molecular iodine serves as an oxidant, while its reduced form, hydrogen iodide, activates the vinyl ether. The redox reaction between these iodine species enables the use of a catalytic amount of iodine in this synthetic method.
authors.affiliation: Faculty of Applied Sciences, Ton Duc Thang University, 19 Nguyen Huu Tho Stress, Tan Phong Ward, District 7, Ho Chi Minh City 700000, Vietnam. lethisong@tdt.edu.vn.
authors.forename: Song Thi
authors.initials: ST
authors.lastname: Le
authors.affiliation: School of Environmental Science and Technology, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan. chorogi.max.x@gmail.com.
authors.forename: Chisa
authors.initials: C
authors.lastname: Yasuoka
authors.affiliation: School of Environmental Science and Technology, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan. asahara.haruyasu@kochi-tech.ac.jp.|Research Center for Material Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan. asahara.haruyasu@kochi-tech.ac.jp.
authors.forename: Haruyasu
authors.initials: H
authors.lastname: Asahara
authors.affiliation: School of Environmental Science and Technology, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan. nishiwaki.nagatoshi@kochi-tech.ac.jp.|Research Center for Material Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan. nishiwaki.nagatoshi@kochi-tech.ac.jp.
authors.forename: Nagatoshi
authors.initials: N
authors.lastname: Nishiwaki
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D007455:Iodine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011798:Quinaldines / Q000138:chemical synthesis / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000814:Aniline Compounds; D011798:Quinaldines; D014753:Vinyl Compounds; C100195:vinyl ether; D007455:Iodine; C037073:2-methylquinoline
keywords: 2-methylquinoline; aniline; iodine-mediated reaction; redox reaction; vinyl ether