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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...

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Autores principales: Kreisel, Tatjana, Mendel, Marvin, Queen, Adele E., Deckers, Kristina, Hupperich, Daniel, Riegger, Julian, Fricke, Christoph, Schoenebeck, Franziska
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
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.
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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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