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Oxidative Coupling of Aryl Boron Reagents with sp 3 ‐Carbon Nucleophiles: The Enolate Chan–Evans–Lam Reaction
Author(s) -
Moon Patrick J.,
Halperin Heather M.,
Lundgren Rylan J.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201510558
Subject(s) - nucleophile , chemistry , electrophile , aryl , amide , boron , halogen , medicinal chemistry , combinatorial chemistry , reagent , coupling reaction , methylene , oxidative coupling of methane , oxidative addition , organic chemistry , catalysis , alkyl
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 S N 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.