Photochemical reactions of a diamidocarbene: cyclopropanation of bromonaphthalene, addition to pyridine, and activation of sp(3) C–H bonds

We report unprecedented photochemistry for the diamidocarbene 1. Described within are the double cyclopropanation of 1-bromonaphthalene, the double addition to pyridine, and remarkably, the insertion into the unactivated sp(3) C–H bonds of cyclohexane, tetramethylsilane, and n-pentane to give compou...

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Detalles Bibliográficos
Autores principales: Perera, Tharushi A., Taylor, William V., Gildner, M. Brenton, Reinheimer, Eric W., Ito, Sho, Nelson, Anna, Yost, Shane R., Hudnall, Todd W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10370591/
https://www.ncbi.nlm.nih.gov/pubmed/37502328
http://dx.doi.org/10.1039/d2sc05122b
Descripción
Sumario:We report unprecedented photochemistry for the diamidocarbene 1. Described within are the double cyclopropanation of 1-bromonaphthalene, the double addition to pyridine, and remarkably, the insertion into the unactivated sp(3) C–H bonds of cyclohexane, tetramethylsilane, and n-pentane to give compounds 2–6, respectively. All compounds have been fully characterized, and the solid state structure of 4 was obtained using single crystal electron diffraction.

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