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Modular Generation of (Iodinated) Polyarenes Using Triethylgermane as Orthogonal Masking Group
While the modular construction of molecules from suitable building blocks is a powerful means to more rapidly generate a diversity of molecules than through customized syntheses, the further evolution of the underlying coupling methodology is key to realize widespread applications. We herein disclos...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9314983/ https://www.ncbi.nlm.nih.gov/pubmed/35263493 http://dx.doi.org/10.1002/anie.202201475 |
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author | Kreisel, Tatjana Mendel, Marvin Queen, Adele E. Deckers, Kristina Hupperich, Daniel Riegger, Julian Fricke, Christoph Schoenebeck, Franziska |
author_facet | Kreisel, Tatjana Mendel, Marvin Queen, Adele E. Deckers, Kristina Hupperich, Daniel Riegger, Julian Fricke, Christoph Schoenebeck, Franziska |
author_sort | Kreisel, Tatjana |
collection | PubMed |
description | While the modular construction of molecules from suitable building blocks is a powerful means to more rapidly generate a diversity of molecules than through customized syntheses, the further evolution of the underlying coupling methodology is key to realize widespread applications. We herein disclose a complementary modular coupling approach to the widely employed Suzuki coupling strategy of boron containing precursors, which relies on organogermane containing building blocks as key orthogonal functionality and an electrophilic (rather than nucleophilic) unmasking event paired with air‐stable Pd(I) dimer based bond construction. This allows to significantly shorten the reaction times for the iterative coupling steps and/or to close gaps in the accessible compound space, enabling straightforward access also to iodinated compounds. |
format | Online Article Text |
id | pubmed-9314983 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-93149832022-07-30 Modular Generation of (Iodinated) Polyarenes Using Triethylgermane as Orthogonal Masking Group Kreisel, Tatjana Mendel, Marvin Queen, Adele E. Deckers, Kristina Hupperich, Daniel Riegger, Julian Fricke, Christoph Schoenebeck, Franziska Angew Chem Int Ed Engl Research Articles While the modular construction of molecules from suitable building blocks is a powerful means to more rapidly generate a diversity of molecules than through customized syntheses, the further evolution of the underlying coupling methodology is key to realize widespread applications. We herein disclose a complementary modular coupling approach to the widely employed Suzuki coupling strategy of boron containing precursors, which relies on organogermane containing building blocks as key orthogonal functionality and an electrophilic (rather than nucleophilic) unmasking event paired with air‐stable Pd(I) dimer based bond construction. This allows to significantly shorten the reaction times for the iterative coupling steps and/or to close gaps in the accessible compound space, enabling straightforward access also to iodinated compounds. John Wiley and Sons Inc. 2022-03-21 2022-05-09 /pmc/articles/PMC9314983/ /pubmed/35263493 http://dx.doi.org/10.1002/anie.202201475 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ (https://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. |
spellingShingle | Research Articles Kreisel, Tatjana Mendel, Marvin Queen, Adele E. Deckers, Kristina Hupperich, Daniel Riegger, Julian Fricke, Christoph Schoenebeck, Franziska Modular Generation of (Iodinated) Polyarenes Using Triethylgermane as Orthogonal Masking Group |
title | Modular Generation of (Iodinated) Polyarenes Using Triethylgermane as Orthogonal Masking Group |
title_full | Modular Generation of (Iodinated) Polyarenes Using Triethylgermane as Orthogonal Masking Group |
title_fullStr | Modular Generation of (Iodinated) Polyarenes Using Triethylgermane as Orthogonal Masking Group |
title_full_unstemmed | Modular Generation of (Iodinated) Polyarenes Using Triethylgermane as Orthogonal Masking Group |
title_short | Modular Generation of (Iodinated) Polyarenes Using Triethylgermane as Orthogonal Masking Group |
title_sort | modular generation of (iodinated) polyarenes using triethylgermane as orthogonal masking group |
topic | Research Articles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9314983/ https://www.ncbi.nlm.nih.gov/pubmed/35263493 http://dx.doi.org/10.1002/anie.202201475 |
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