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Synthesis of Quaternary and Tertiary Carbon-Substituted Arenes by Lewis Base Promoted Site-Selective Coupling with Allylic Nucleophiles
Authors:Hawa Keita  Prof Simon J Meek
Institution:Department of Chemistry, University of North Carolina at Chapel Hill, 27599-3290 Chapel Hill, NC, USA
Abstract:A practical method for the preparation of quaternary and tertiary allyl-substituted heteroarenes by site-selective couplings of heteroaryl nitriles and allylic nucleophiles is disclosed. Transformations utilize readily accessible stable reagents, proceed in the presence of a Lewis base activator, and undergo aryl-C(sp3) quaternary and tertiary carbon formation with high γ-selectivity (up to >98 : 2 γ : α).
Keywords:Allylation  Arene Coupling  Heterocycle  Organoboron  Quaternary Carbon
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