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Oxidative Coupling of Aryl Boron Reagents with sp(3)-Carbon Nucleophiles: The Enolate Chan-Evans-Lam Reaction
Patrick J Moon1, Heather M Halperin1, Rylan J Lundgren2
1Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada.
Abstract:
Reported is a versatile new oxidative method for the arylation of activated methylene species. Under mild reaction conditions (RT to 40 °C), Cu(OTf)2 mediates the selective coupling of functionalized aryl boron species with a variety of stabilized sp(3) -nucleophiles. Tertiary malonates and amido esters can be employed as substrates to generate quaternary centers. Complementing either traditional cross-coupling or SN Ar protocols, the transformation is chemoselective in the presence of halogen electrophiles, including aryl bromides and iodides. Substrates bearing amide, sulfonyl, and phosphonyl groups, which are not amenable to coupling under mild Hurtley-type conditions, are suitable reaction partners.
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