Simple strategies for decarboxylative functionalizations of electron-deficient benzoic acids via using Cu(I) as promoter and electron-rich ones by employing Pd(II) as catalyst under aerobic conditions have been established, which lead to smooth synthesis of aryl halides (-I, Br, and Cl) through the decarboxylative functionalization of benzoic acids with readily available halogen sources CuX (X = I, Br, Cl), and easy preparation of benzonitriles from decarboxylative cyanation of aryl carboxylic acids with nontoxic and low-cost K4Fe(CN)6 under an oxygen atmosphere for the first time.
Allenes are the simplest class of cumulenes, possessing unique physical and chemical properties. These structural units are widely used as valuable synthetic intermediates in organic synthesis, as well as the...
Heterocyclic compounds are important organic compounds and have emerged as key scaffolds in numerous drugs, natural products, vitamins, biologically and pharmaceutically active compounds. Over the past few decades, the development of versatile methodologies employing propargylic alcohols as synthons for the construction of heterocyclic skeletons has attracted great attention from synthetic chemists. In this review, recent developments in the cascade cyclization of propargylic alcohols with diverse nucleophiles to construct heterocyclic compounds are summarized. According to the types of nucleophiles, these reactions can be divided into four categories: 1) Reactions involving C‐nucleophiles to capture allenyl carbocation; 2) Reactions involving O, S‐nucleophiles to capture allenyl carbocation; 3) Reactions involving N, P‐nucleophiles to capture allenyl carbocation; 4) Reactions involving halo‐nucleophiles to capture allenyl carbocation.
Aromatic N-heterocycles such as quinolines, isoquinolines, and indolines are synthesized via sodium tert-butoxidepromoted oxidative dehydrogenation of the saturated heterocycles in DMSO solution. This reaction proceeds under mild reaction conditions and has a good functional group tolerance. Mechanistic studies suggest a radical pathway involving hydrogen abstraction of dimsyl radicals from the N−H bond or α-C−H of the substrates and subsequent oxidation of the nitrogen or α-aminoalkyl radicals.
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