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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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
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author Perera, Tharushi A.
Taylor, William V.
Gildner, M. Brenton
Reinheimer, Eric W.
Ito, Sho
Nelson, Anna
Yost, Shane R.
Hudnall, Todd W.
author_facet Perera, Tharushi A.
Taylor, William V.
Gildner, M. Brenton
Reinheimer, Eric W.
Ito, Sho
Nelson, Anna
Yost, Shane R.
Hudnall, Todd W.
author_sort Perera, Tharushi A.
collection PubMed
description 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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spelling pubmed-103705912023-07-27 Photochemical reactions of a diamidocarbene: cyclopropanation of bromonaphthalene, addition to pyridine, and activation of sp(3) C–H bonds Perera, Tharushi A. Taylor, William V. Gildner, M. Brenton Reinheimer, Eric W. Ito, Sho Nelson, Anna Yost, Shane R. Hudnall, Todd W. Chem Sci Chemistry 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. The Royal Society of Chemistry 2023-05-10 /pmc/articles/PMC10370591/ /pubmed/37502328 http://dx.doi.org/10.1039/d2sc05122b Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Perera, Tharushi A.
Taylor, William V.
Gildner, M. Brenton
Reinheimer, Eric W.
Ito, Sho
Nelson, Anna
Yost, Shane R.
Hudnall, Todd W.
Photochemical reactions of a diamidocarbene: cyclopropanation of bromonaphthalene, addition to pyridine, and activation of sp(3) C–H bonds
title Photochemical reactions of a diamidocarbene: cyclopropanation of bromonaphthalene, addition to pyridine, and activation of sp(3) C–H bonds
title_full Photochemical reactions of a diamidocarbene: cyclopropanation of bromonaphthalene, addition to pyridine, and activation of sp(3) C–H bonds
title_fullStr Photochemical reactions of a diamidocarbene: cyclopropanation of bromonaphthalene, addition to pyridine, and activation of sp(3) C–H bonds
title_full_unstemmed Photochemical reactions of a diamidocarbene: cyclopropanation of bromonaphthalene, addition to pyridine, and activation of sp(3) C–H bonds
title_short Photochemical reactions of a diamidocarbene: cyclopropanation of bromonaphthalene, addition to pyridine, and activation of sp(3) C–H bonds
title_sort photochemical reactions of a diamidocarbene: cyclopropanation of bromonaphthalene, addition to pyridine, and activation of sp(3) c–h bonds
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10370591/
https://www.ncbi.nlm.nih.gov/pubmed/37502328
http://dx.doi.org/10.1039/d2sc05122b
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