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C-8-Selective Allylation of Quinoline: A Case Study of β-Hydride vs β-Hydroxy Elimination
Deepti Kalsi1, Roshayed A Laskar1, Nagaraju Barsu1
1Fine Chemical Laboratory, Department of Chemistry, Indian Institute of Technology Kanpur , Kanpur, Uttar Pradesh 208016, India.
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.
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