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Rh(III)‐Catalyzed C−H Activation of Aryl Hydroxamates for the Synthesis of Isoindolinones
Rh(III)‐catalyzed C−H functionalization reaction yielding isoindolinones from aryl hydroxamates and ortho‐substituted styrenes is reported. The reaction proceeds smoothly under mild conditions at room temperature, and tolerates a range of functional groups. Experimental and computational investigati...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7496876/ https://www.ncbi.nlm.nih.gov/pubmed/32428319 http://dx.doi.org/10.1002/chem.202002384 |
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author | Shaaban, Saad Davies, Caitlin Merten, Christian Flegel, Jana Otte, Felix Strohmann, Carsten Waldmann, Herbert |
author_facet | Shaaban, Saad Davies, Caitlin Merten, Christian Flegel, Jana Otte, Felix Strohmann, Carsten Waldmann, Herbert |
author_sort | Shaaban, Saad |
collection | PubMed |
description | Rh(III)‐catalyzed C−H functionalization reaction yielding isoindolinones from aryl hydroxamates and ortho‐substituted styrenes is reported. The reaction proceeds smoothly under mild conditions at room temperature, and tolerates a range of functional groups. Experimental and computational investigations support that the high regioselectivity observed for these substrates results from the presence of an ortho‐substituent embedded in the styrene. The resulting isoindolinones are valuable building blocks for the synthesis of bioactive compounds. They provide easy access to the natural‐product‐like compounds, isoindolobenzazepines, in a one‐pot two‐step reaction. Selected isoindolinones inhibited Hedgehog (Hh)‐dependent differentiation of multipotent murine mesenchymal progenitor stem cells into osteoblasts. |
format | Online Article Text |
id | pubmed-7496876 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-74968762020-09-25 Rh(III)‐Catalyzed C−H Activation of Aryl Hydroxamates for the Synthesis of Isoindolinones Shaaban, Saad Davies, Caitlin Merten, Christian Flegel, Jana Otte, Felix Strohmann, Carsten Waldmann, Herbert Chemistry Communications Rh(III)‐catalyzed C−H functionalization reaction yielding isoindolinones from aryl hydroxamates and ortho‐substituted styrenes is reported. The reaction proceeds smoothly under mild conditions at room temperature, and tolerates a range of functional groups. Experimental and computational investigations support that the high regioselectivity observed for these substrates results from the presence of an ortho‐substituent embedded in the styrene. The resulting isoindolinones are valuable building blocks for the synthesis of bioactive compounds. They provide easy access to the natural‐product‐like compounds, isoindolobenzazepines, in a one‐pot two‐step reaction. Selected isoindolinones inhibited Hedgehog (Hh)‐dependent differentiation of multipotent murine mesenchymal progenitor stem cells into osteoblasts. John Wiley and Sons Inc. 2020-07-21 2020-08-21 /pmc/articles/PMC7496876/ /pubmed/32428319 http://dx.doi.org/10.1002/chem.202002384 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Communications Shaaban, Saad Davies, Caitlin Merten, Christian Flegel, Jana Otte, Felix Strohmann, Carsten Waldmann, Herbert Rh(III)‐Catalyzed C−H Activation of Aryl Hydroxamates for the Synthesis of Isoindolinones |
title | Rh(III)‐Catalyzed C−H Activation of Aryl Hydroxamates for the Synthesis of Isoindolinones |
title_full | Rh(III)‐Catalyzed C−H Activation of Aryl Hydroxamates for the Synthesis of Isoindolinones |
title_fullStr | Rh(III)‐Catalyzed C−H Activation of Aryl Hydroxamates for the Synthesis of Isoindolinones |
title_full_unstemmed | Rh(III)‐Catalyzed C−H Activation of Aryl Hydroxamates for the Synthesis of Isoindolinones |
title_short | Rh(III)‐Catalyzed C−H Activation of Aryl Hydroxamates for the Synthesis of Isoindolinones |
title_sort | rh(iii)‐catalyzed c−h activation of aryl hydroxamates for the synthesis of isoindolinones |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7496876/ https://www.ncbi.nlm.nih.gov/pubmed/32428319 http://dx.doi.org/10.1002/chem.202002384 |
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