Carbon-based leaving group in substitution reactions: functionalization of sp3-hybridized quaternary and tertiary benzylic carbon centers.

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 Csp3–Csp3 bonds into Csp3–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%).