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- W3005200276 abstract "A three-component Pd-catalyzed coupling of ynamides, aryl diazonium salts, and aryl boronic acids for the synthesis of novel triaryl-substituted enamides is described. This transformation represents the first example of an umpolung regioselective unsymmetrical syn-1,2-diarylation/aryl-olefination of ynamides. The aryl moieties of the diazonium salt (electrophile) and boronic acid (nucleophile) are explicitly incorporated in the electrophilic α- and nucleophilic β-position, respectively, of the ynamide, resulting in a single isomer of the N-bearing tetrasubstituted olefin. The scope is broad (68 examples), showing excellent functional-group tolerance. DFT calculations substantiate the rationale of the mechanistic cycle and the regioselectivity. The chemoselectivity and synthetic potential of the enamide products were also studied." @default.
- W3005200276 created "2020-02-14" @default.
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- W3005200276 date "2020-03-02" @default.
- W3005200276 modified "2023-09-30" @default.
- W3005200276 title "Keteniminium‐Driven Umpolung Difunctionalization of Ynamides" @default.
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- W3005200276 doi "https://doi.org/10.1002/anie.201915522" @default.
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