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 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%).
Department of Chemistry, University of Waterloo, Waterloo, Ontario, N2L 3G1, Canada.
Stuart J
SJ
Mahoney
Tiantong
T
Lou
Ganna
G
Bondarenko
Eric
E
Fillion