Carbon-based leaving group in substitution reactions: functionalization of sp3-hybridized quaternary and tertiary benzylic carbon centers |
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Authors: | Mahoney Stuart J Lou Tiantong Bondarenko Ganna Fillion Eric |
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Affiliation: | Department of Chemistry, University of Waterloo, Waterloo, Ontario, N2L 3G1, Canada. |
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Abstract: | Lewis acid promoted substitution reactions employing Meldrum's acid and 5-methyl Meldrum's acid as carbon-based leaving groups are described which transform unstrained quaternary and tertiary benzylic C(sp(3))-C(sp(3)) bonds into C(sp(3))-X bonds (X = C, H, N). Importantly, this reaction has a broad scope in terms of both suitable substrates and nucleophiles with good to excellent yields obtained (typically >90%). |
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