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 C-H bonds of cyclohexane, tetramethylsilane, and -pentane to give compounds...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2023-07, Vol.14 (29), p.7867-7874
Main Authors: Perera, Tharushi A, Taylor, William V, Gildner, M Brenton, Reinheimer, Eric W, Ito, Sho, Nelson, Anna, Yost, Shane R, Hudnall, Todd W
Format: Article
Language:English
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Summary: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 C-H bonds of cyclohexane, tetramethylsilane, and -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.
ISSN:2041-6520
2041-6539
DOI:10.1039/D2SC05122B