An
efficient strategy toward 4-arylquinolines and 4-arylpyrimidines from
readily available precursors is described. Oxidative annulation promoted
by K2S2O8 involving anilines, aryl
ketones, and DMSO as a methine (CH−) equivalent leads
to 4-arylquinolines via a cascade that entails generation of a sulfenium
ion, subsequent C–N and C–C bond formations, and cyclization.
The application of this strategy to the activation of acetophenone–formamide
conjugates toward the synthesis of 4-arylpyrimidines is also described.
The activation of ethyl bromofluoroacetate employing a visible light mediated, Eosin Y catalyzed photoredox transformation is reported. Using indoles and anilines as nucleophiles, the reaction leads to the formation of two C(sp(2))-C(sp(3)) bonds resulting in an efficient synthesis of bisindolyl and bisanilinoyl acetate derivatives. Application of this method to the direct synthesis of unsymmetrical diarylacetates featuring indoles and N-substituted anilines was also demonstrated.
Ethyl bromofluoroacetate has been developed as a precursor for the convenient synthesis of unsymmetrical α,α-diarylacetates featuring indoles, anilines, and other electron-rich aromatics. In conjunction with a mild Lewis acid catalyzed C-N → C-C exchange, intermediate arylglycines can be synthesized and transformed into α,α-diarylacetates in a one-pot protocol, resulting in a net diarylation reaction exhibiting a wide scope. In the context of diarylacetates, the synthetic equivalence of the fluorinated reagent with α-nitro-α-diazo carbonyls was established.
A ligand‐free, copper‐catalyzed divergent route toward oxindoles and isatins from a common α‐diazoanilide precursor is reported. The reaction offers a broad scope, provides an efficient catalytic synthesis protocol that is mild, involves only oxygen as an oxidant, and unique in its ability to provide either oxindoles or isatins by exploiting oxygenase‐type reactivity that does not require peroxide additives or sacrificial aldehydes. The versatility of this reaction manifold has been demonstrated by synthesizing an analog of sunitinib, an FDA approved drug for renal cell carcinoma and imatinib‐resistant gastrointestinal stromal tumor.
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