DNA-Compatible Suzuki-Miyaura Cross-Coupling Reaction of Aryl Iodides With (Hetero)Aryl Boronic Acids for DNA-Encoded Libraries

An efficient method for the C-C bond formation via water soluble Na(2)PdCl(4)/sSPhos mediated Suzuki-Miyaura cross-coupling reaction of DNA-conjugated aryl iodide with (het)aryl boronic acids has been developed. This reaction proceeds at 37°C in water and acetonitrile (4:1) system. We also demonstra...

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Autores principales: Siripuram, Vijay Kumar, Sunkari, Yashoda Krishna, Nguyen, Thu-Lan, Flajolet, Marc
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9237475/
https://www.ncbi.nlm.nih.gov/pubmed/35774858
http://dx.doi.org/10.3389/fchem.2022.894603
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author Siripuram, Vijay Kumar
Sunkari, Yashoda Krishna
Nguyen, Thu-Lan
Flajolet, Marc
author_facet Siripuram, Vijay Kumar
Sunkari, Yashoda Krishna
Nguyen, Thu-Lan
Flajolet, Marc
author_sort Siripuram, Vijay Kumar
collection PubMed
description An efficient method for the C-C bond formation via water soluble Na(2)PdCl(4)/sSPhos mediated Suzuki-Miyaura cross-coupling reaction of DNA-conjugated aryl iodide with (het)aryl boronic acids has been developed. This reaction proceeds at 37°C in water and acetonitrile (4:1) system. We also demonstrated that numerous aromatic and heteroaromatic boronic acids of different electronic natures, and harboring various functional groups, were highly compatible providing the desired coupling products in good to excellent yields. This DNA-compatible Suzuki-Miyaura cross-coupling reaction has strong potential to construct DNA-Encoded Libraries (DELs) in the context of drug discovery.
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spelling pubmed-92374752022-06-29 DNA-Compatible Suzuki-Miyaura Cross-Coupling Reaction of Aryl Iodides With (Hetero)Aryl Boronic Acids for DNA-Encoded Libraries Siripuram, Vijay Kumar Sunkari, Yashoda Krishna Nguyen, Thu-Lan Flajolet, Marc Front Chem Chemistry An efficient method for the C-C bond formation via water soluble Na(2)PdCl(4)/sSPhos mediated Suzuki-Miyaura cross-coupling reaction of DNA-conjugated aryl iodide with (het)aryl boronic acids has been developed. This reaction proceeds at 37°C in water and acetonitrile (4:1) system. We also demonstrated that numerous aromatic and heteroaromatic boronic acids of different electronic natures, and harboring various functional groups, were highly compatible providing the desired coupling products in good to excellent yields. This DNA-compatible Suzuki-Miyaura cross-coupling reaction has strong potential to construct DNA-Encoded Libraries (DELs) in the context of drug discovery. Frontiers Media S.A. 2022-06-14 /pmc/articles/PMC9237475/ /pubmed/35774858 http://dx.doi.org/10.3389/fchem.2022.894603 Text en Copyright © 2022 Siripuram, Sunkari, Nguyen and Flajolet. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Siripuram, Vijay Kumar
Sunkari, Yashoda Krishna
Nguyen, Thu-Lan
Flajolet, Marc
DNA-Compatible Suzuki-Miyaura Cross-Coupling Reaction of Aryl Iodides With (Hetero)Aryl Boronic Acids for DNA-Encoded Libraries
title DNA-Compatible Suzuki-Miyaura Cross-Coupling Reaction of Aryl Iodides With (Hetero)Aryl Boronic Acids for DNA-Encoded Libraries
title_full DNA-Compatible Suzuki-Miyaura Cross-Coupling Reaction of Aryl Iodides With (Hetero)Aryl Boronic Acids for DNA-Encoded Libraries
title_fullStr DNA-Compatible Suzuki-Miyaura Cross-Coupling Reaction of Aryl Iodides With (Hetero)Aryl Boronic Acids for DNA-Encoded Libraries
title_full_unstemmed DNA-Compatible Suzuki-Miyaura Cross-Coupling Reaction of Aryl Iodides With (Hetero)Aryl Boronic Acids for DNA-Encoded Libraries
title_short DNA-Compatible Suzuki-Miyaura Cross-Coupling Reaction of Aryl Iodides With (Hetero)Aryl Boronic Acids for DNA-Encoded Libraries
title_sort dna-compatible suzuki-miyaura cross-coupling reaction of aryl iodides with (hetero)aryl boronic acids for dna-encoded libraries
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9237475/
https://www.ncbi.nlm.nih.gov/pubmed/35774858
http://dx.doi.org/10.3389/fchem.2022.894603
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