Iron-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Aromatic Diamines: Selective Synthesis of 1,2-Disubstituted Benzimidazoles

Benzimidazoles are important N-heteroaromatic compounds with various biological activities and pharmacological applications. Herein, we present the first iron-catalyzed selective synthesis of 1,2-disubstituted benzimidazoles via acceptorless dehydrogenative coupling of primary alcohols with aromatic...

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Autores principales: Putta, Ramachandra Reddy, Chun, Simin, Lee, Seok Beom, Oh, Dong-Chan, Hong, Suckchang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7317090/
https://www.ncbi.nlm.nih.gov/pubmed/32637390
http://dx.doi.org/10.3389/fchem.2020.00429
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author Putta, Ramachandra Reddy
Chun, Simin
Lee, Seok Beom
Oh, Dong-Chan
Hong, Suckchang
author_facet Putta, Ramachandra Reddy
Chun, Simin
Lee, Seok Beom
Oh, Dong-Chan
Hong, Suckchang
author_sort Putta, Ramachandra Reddy
collection PubMed
description Benzimidazoles are important N-heteroaromatic compounds with various biological activities and pharmacological applications. Herein, we present the first iron-catalyzed selective synthesis of 1,2-disubstituted benzimidazoles via acceptorless dehydrogenative coupling of primary alcohols with aromatic diamines. The tricarbonyl (η(4)-cyclopentadienone) iron complex catalyzed dehydrogenative cyclization, releasing water and hydrogen gas as by-products. The earth abundance and low toxicity of iron metal enable the provision of an eco-friendly and efficient catalytic method for the synthesis of benzimidazoles.
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spelling pubmed-73170902020-07-06 Iron-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Aromatic Diamines: Selective Synthesis of 1,2-Disubstituted Benzimidazoles Putta, Ramachandra Reddy Chun, Simin Lee, Seok Beom Oh, Dong-Chan Hong, Suckchang Front Chem Chemistry Benzimidazoles are important N-heteroaromatic compounds with various biological activities and pharmacological applications. Herein, we present the first iron-catalyzed selective synthesis of 1,2-disubstituted benzimidazoles via acceptorless dehydrogenative coupling of primary alcohols with aromatic diamines. The tricarbonyl (η(4)-cyclopentadienone) iron complex catalyzed dehydrogenative cyclization, releasing water and hydrogen gas as by-products. The earth abundance and low toxicity of iron metal enable the provision of an eco-friendly and efficient catalytic method for the synthesis of benzimidazoles. Frontiers Media S.A. 2020-06-19 /pmc/articles/PMC7317090/ /pubmed/32637390 http://dx.doi.org/10.3389/fchem.2020.00429 Text en Copyright © 2020 Putta, Chun, Lee, Oh and Hong. http://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
Putta, Ramachandra Reddy
Chun, Simin
Lee, Seok Beom
Oh, Dong-Chan
Hong, Suckchang
Iron-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Aromatic Diamines: Selective Synthesis of 1,2-Disubstituted Benzimidazoles
title Iron-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Aromatic Diamines: Selective Synthesis of 1,2-Disubstituted Benzimidazoles
title_full Iron-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Aromatic Diamines: Selective Synthesis of 1,2-Disubstituted Benzimidazoles
title_fullStr Iron-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Aromatic Diamines: Selective Synthesis of 1,2-Disubstituted Benzimidazoles
title_full_unstemmed Iron-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Aromatic Diamines: Selective Synthesis of 1,2-Disubstituted Benzimidazoles
title_short Iron-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Aromatic Diamines: Selective Synthesis of 1,2-Disubstituted Benzimidazoles
title_sort iron-catalyzed acceptorless dehydrogenative coupling of alcohols with aromatic diamines: selective synthesis of 1,2-disubstituted benzimidazoles
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7317090/
https://www.ncbi.nlm.nih.gov/pubmed/32637390
http://dx.doi.org/10.3389/fchem.2020.00429
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