title: Mechanistic investigation of the cobalt-catalyzed selective conversion of diallylanilines to quinolines involving C-N and C-H activations.
abstract: 2,3-Substituted quinolines were readily prepared from diallylanilines in good yields under mild conditions by using Co2(CO)(8) as catalyst. Regioselectivity has been explored by examining a series of electron-donating and electron-withdrawing functional groups at ortho, meta, and para positions of the diallylanilines. The results show that both steric and electronic effects influence the isolated yields. Electron-withdrawing groups inhibit the reaction. Solvent effects, temperature effects, and catalyst loadings have also been investigated. Isotopic labeling experiments were devised to permit delineation of the mechanism of reaction.
authors: Department of Chemistry, University of Rochester, Rochester, New York 14627, USA.
authors: Ling
authors: L
authors: Li
authors: William D
authors: WD
authors: Jones
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry; D003903:Deuterium; D011804:Quinolines / Q000138:chemical synthesis*
chemical_list: D000498:Allyl Compounds; D000814:Aniline Compounds; D011804:Quinolines; D003035:Cobalt; D003903:Deuterium