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Molecules
Volume 25
Issue 2
10.3390/molecules25020361
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Article

Synthesis of Elaborate Benzofuran-2-Carboxamide Derivatives through a Combination of 8-Aminoquinoline Directed C–H Arylation and Transamidation Chemistry

by
Michael Oschmann
†,
Linus Johansson Holm
†,
Monireh Pourghasemi-Lati
and
Oscar Verho
*
Arrhenius Laboratory, Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden
*
Author to whom correspondence should be addressed.
†
Authors contributed equally to this manuscript.
Molecules 2020, 25(2), 361; https://doi.org/10.3390/molecules25020361
Received: 20 December 2019 / Revised: 9 January 2020 / Accepted: 13 January 2020 / Published: 15 January 2020
(This article belongs to the Special Issue Recent Advances in C-H Functionalization)
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Abstract

Herein, we present a short and highly modular synthetic route that involves 8-aminoquinoline directed C–H arylation and transamidation chemistry, and which enables access to a wide range of elaborate benzofuran-2-carboxamides. For the directed C–H arylation reactions, Pd catalysis was used to install a wide range of aryl and heteroaryl substituents at the C3 position of the benzofuran scaffold in high efficiency. Directing group cleavage and further diversification of the C3-arylated benzofuran products were then achieved in a single synthetic operation through the utilization of a one-pot, two-step transamidation procedure, which proceeded via the intermediate N-acyl-Boc-carbamates. Given the high efficiency and modularity of this synthetic strategy, it constitutes a very attractive method for generating structurally diverse collections of benzofuran derivatives for small molecule screening campaigns. View Full-Text
Keywords: palladium; C–H functionalization; 8-aminoquinoline; benzofuran; transamidation palladium; C–H functionalization; 8-aminoquinoline; benzofuran; transamidation
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited

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    Doi: 10.5281/zenodo.3603317
    Link: https://doi.org/10.5281/zenodo.3603317
    Description: Supporting Information for "Synthesis of elaborate benzofuran-2-carboxamide derivatives through a combination of 8-aminoquinoline directed C–H arylations and transamidations".
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MDPI and ACS Style

Oschmann, M.; Johansson Holm, L.; Pourghasemi-Lati, M.; Verho, O. Synthesis of Elaborate Benzofuran-2-Carboxamide Derivatives through a Combination of 8-Aminoquinoline Directed C–H Arylation and Transamidation Chemistry. Molecules 2020, 25, 361. https://doi.org/10.3390/molecules25020361

AMA Style

Oschmann M, Johansson Holm L, Pourghasemi-Lati M, Verho O. Synthesis of Elaborate Benzofuran-2-Carboxamide Derivatives through a Combination of 8-Aminoquinoline Directed C–H Arylation and Transamidation Chemistry. Molecules. 2020; 25(2):361. https://doi.org/10.3390/molecules25020361

Chicago/Turabian Style

Oschmann, Michael, Linus Johansson Holm, Monireh Pourghasemi-Lati, and Oscar Verho. 2020. "Synthesis of Elaborate Benzofuran-2-Carboxamide Derivatives through a Combination of 8-Aminoquinoline Directed C–H Arylation and Transamidation Chemistry" Molecules 25, no. 2: 361. https://doi.org/10.3390/molecules25020361

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