Mechanistic investigation of the cobalt-catalyzed selective conversion of diallylanilines to quinolines involving C-N and C-H activations.
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.
Li
Ling
L
Department of Chemistry, University of Rochester, Rochester, New York 14627, USA.
Jones
William D
WD
D000498:Allyl Compounds / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry; D003903:Deuterium; D011804:Quinolines / Q000138:chemical synthesis*
D000498:Allyl Compounds; D000814:Aniline Compounds; D011804:Quinolines; D003035:Cobalt; D003903:Deuterium