Palladium-Catalyzed Insertion of <i>N</i>‑tosylhydrazones and Trapping with Carbon Nucleophiles

A Pd-catalyzed three-component cross-coupling reaction of vinyl iodide, <i>N</i>-tosylhydrazone, and carbon nucleophiles is reported, and a one-pot procedure is also developed. The cross-coupling is proposed to proceed through a palladium–carbene migratory insertion, carbopalladation other than classic palladium–carbene migratory insertion, and β-H elimination. Moreover, the reaction proceeds under mild conditions and with high stereoselectivity

Brønsted Acid Catalyzed and NIS-Promoted Cyclization of Diynones: Selective Synthesis of 4‑Pyrone, 4‑Pyridone, and 3‑Pyrrolone Derivatives

Brønsted acid catalyzed tandem cyclization was found to be highly effective for the preparation of a series of polysubstituted 4-pyrones from diynones (yield up to 99%). 4-Pyridone and 3-pyrrolone derivatives were also selectively synthesized by employing NIS and/or Brønsted acid. NIS as an electrophilic reagent could promote these reactions efficiently and rapidly under very mild reaction conditions

Brønsted Acid Catalyzed and NIS-Promoted Cyclization of Diynones: Selective Synthesis of 4‑Pyrone, 4‑Pyridone, and 3‑Pyrrolone Derivatives

Brønsted acid catalyzed tandem cyclization was found to be highly effective for the preparation of a series of polysubstituted 4-pyrones from diynones (yield up to 99%). 4-Pyridone and 3-pyrrolone derivatives were also selectively synthesized by employing NIS and/or Brønsted acid. NIS as an electrophilic reagent could promote these reactions efficiently and rapidly under very mild reaction conditions

Brønsted Acid Catalyzed and NIS-Promoted Cyclization of Diynones: Selective Synthesis of 4‑Pyrone, 4‑Pyridone, and 3‑Pyrrolone Derivatives

Brønsted acid catalyzed tandem cyclization was found to be highly effective for the preparation of a series of polysubstituted 4-pyrones from diynones (yield up to 99%). 4-Pyridone and 3-pyrrolone derivatives were also selectively synthesized by employing NIS and/or Brønsted acid. NIS as an electrophilic reagent could promote these reactions efficiently and rapidly under very mild reaction conditions

Brønsted Acid Catalyzed and NIS-Promoted Cyclization of Diynones: Selective Synthesis of 4‑Pyrone, 4‑Pyridone, and 3‑Pyrrolone Derivatives

Brønsted acid catalyzed tandem cyclization was found to be highly effective for the preparation of a series of polysubstituted 4-pyrones from diynones (yield up to 99%). 4-Pyridone and 3-pyrrolone derivatives were also selectively synthesized by employing NIS and/or Brønsted acid. NIS as an electrophilic reagent could promote these reactions efficiently and rapidly under very mild reaction conditions

Palladium-Catalyzed Acylation/Alkenylation of Aryl Iodide: A Domino Approach Based on the Catellani–Lautens Reaction

A new palladium-catalyzed three-component coupling involving acylation/alkenylation of aryl iodide is reported. The reaction was carried out with readily available starting materials and gave the ortho-acylated styrene in moderate to good yields. Compared with previous Catellani–Lautens reactions, this reaction is the first example of introducing an acyl group at the ortho position of aryl iodides. The proposed Pd^IV complex, generated via oxidative addition of the carboxylic anhydrides, is a key intermediate for this transformation

Palladium-Catalyzed/Norbornene-Mediated <i>ortho</i>-Amination/<i>N</i>‑Tosylhydrazone Insertion Reaction: An Approach to the Synthesis of <i>ortho</i>-Aminated Vinylarenes

<i>ortho</i>-Aminated vinylarene derivatives were obtained via a reaction of aryl iodides, <i>N</i>-benzoyloxyamines, and <i>N</i>-tosylhydrazones. This approach involves a palladium-catalyzed, norbornene-mediated <i>ortho</i>-amination/<i>N</i>-tosylhydrazone insertion reaction. In this transformation, one C–N bond and one C–C bond are formed and an amine group is introduced at the <i>ortho</i> position successfully