title: C-8-Selective Allylation of Quinoline: A Case Study of β-Hydride vs β-Hydroxy Elimination.
abstract: An unprecedented C(8)-H bond allylation of quinoline with allyl carbonate and allyl alcohol catalyzed by Cp*Co(III) using a traceless directing group via β-oxygen and β-hydroxy elimination is described. This site-selective allylation reaction proceeds smoothly with various functional group tolerance including quinoxaline and phenanthridine. Under the nonoxidative reaction conditions, the difference in selectivity between Rh(III) and Co(III), which proceeds through β-hydride and β-hydroxy elimination using allyl alcohol, is shown for the first time.
authors.affiliation: Fine Chemical Laboratory, Department of Chemistry, Indian Institute of Technology Kanpur , Kanpur, Uttar Pradesh 208016, India.
authors.forename: Deepti
authors.initials: D
authors.lastname: Kalsi
authors.affiliation: Fine Chemical Laboratory, Department of Chemistry, Indian Institute of Technology Kanpur , Kanpur, Uttar Pradesh 208016, India.
authors.forename: Roshayed A
authors.initials: RA
authors.lastname: Laskar
authors.affiliation: Fine Chemical Laboratory, Department of Chemistry, Indian Institute of Technology Kanpur , Kanpur, Uttar Pradesh 208016, India.
authors.forename: Nagaraju
authors.initials: N
authors.lastname: Barsu
authors.affiliation: Center for Molecular Modelling, Indian Institute of Chemical Technology , Hyderabad 500007, India.
authors.forename: J Richard
authors.initials: JR
authors.lastname: Premkumar
authors.affiliation: Fine Chemical Laboratory, Department of Chemistry, Indian Institute of Technology Kanpur , Kanpur, Uttar Pradesh 208016, India.
authors.forename: Basker
authors.initials: B
authors.lastname: Sundararaju