Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 42, Pages 13826-13829Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b08906
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Funding
- NSERC Canada
- University of Alberta
- SV ChemBioTech
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We report decarboxylative carbonyl alpha-arylation by coupling of arylboron nucleophiles with malonic acid derivatives. This process is enabled by the merger of aerobic oxidative Cu catalysis with decarboxylative enolate interception reminiscent of malonyl-CoA reactivity in polyketide biosynthesis. This method enables the synthesis of monoaryl acetate derivatives containing electrophilic functional groups that are incompatible with existing alpha-arylation reactivity paradigms. The utility of the reaction is demonstrated in drug intermediate synthesis and late-stage functionalization.
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