Modular Synthesis of Multisubstituted Furans through Palladium-Catalyzed Three-Component Condensation of Alkynylbenziodoxoles, Carboxylic Acids, and Imines
Mild and regiocontrolled synthesis of a multisubstituted furan is achieved through Pd(OAc)2-catalyzed room-temperature condensation of an alkynylbenziodoxole, a carboxylic acid, and an enolizable ketimine, which contribute to C1, CO, and C2 fragments, respectively, to the furan skeleton. The reactio...
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sg-ntu-dr.10356-1036932023-02-28T19:27:46Z Modular Synthesis of Multisubstituted Furans through Palladium-Catalyzed Three-Component Condensation of Alkynylbenziodoxoles, Carboxylic Acids, and Imines Wu, Junliang Yoshikai, Naohiko School of Physical and Mathematical Sciences DRNTU::Science::Chemistry Mild and regiocontrolled synthesis of a multisubstituted furan is achieved through Pd(OAc)2-catalyzed room-temperature condensation of an alkynylbenziodoxole, a carboxylic acid, and an enolizable ketimine, which contribute to C1, CO, and C2 fragments, respectively, to the furan skeleton. The reaction tolerates a broad range of functional groups in each of the reaction components, and enables highly modular and flexible synthesis of variously substituted furans. The reaction is particularly effective for the rapid generation of tri- and tetraarylfurans and furan-containing oligoarylenes without relying on conventional cross-coupling chemistry. NRF (Natl Research Foundation, S’pore) Accepted version 2015-10-12T03:20:37Z 2019-12-06T21:18:07Z 2015-10-12T03:20:37Z 2019-12-06T21:18:07Z 2015 2015 Journal Article Wu, J., & Yoshikai, N. (2015). Modular Synthesis of Multisubstituted Furans through Palladium-Catalyzed Three-Component Condensation of Alkynylbenziodoxoles, Carboxylic Acids, and Imines. Angewandte Chemie - International Edition, 54(38), 11107-11111. 1433-7851 https://hdl.handle.net/10356/103693 http://hdl.handle.net/10220/38788 10.1002/anie.201504687 en Angewandte Chemie - International Edition © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the author created version of a work that has been peer reviewed and accepted for publication by Angewandte Chemie - International Edition, WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [http://dx.doi.org/10.1002/anie.201504687]. 5p. application/pdf |
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DRNTU::Science::Chemistry Wu, Junliang Yoshikai, Naohiko Modular Synthesis of Multisubstituted Furans through Palladium-Catalyzed Three-Component Condensation of Alkynylbenziodoxoles, Carboxylic Acids, and Imines |
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Mild and regiocontrolled synthesis of a multisubstituted furan is achieved through Pd(OAc)2-catalyzed room-temperature condensation of an alkynylbenziodoxole, a carboxylic acid, and an enolizable ketimine, which contribute to C1, CO, and C2 fragments, respectively, to the furan skeleton. The reaction tolerates a broad range of functional groups in each of the reaction components, and enables highly modular and flexible synthesis of variously substituted furans. The reaction is particularly effective for the rapid generation of tri- and tetraarylfurans and furan-containing oligoarylenes without relying on conventional cross-coupling chemistry. |
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School of Physical and Mathematical Sciences |
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School of Physical and Mathematical Sciences Wu, Junliang Yoshikai, Naohiko |
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Article |
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Wu, Junliang Yoshikai, Naohiko |
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Wu, Junliang |
title |
Modular Synthesis of Multisubstituted Furans through Palladium-Catalyzed Three-Component Condensation of Alkynylbenziodoxoles, Carboxylic Acids, and Imines |
title_short |
Modular Synthesis of Multisubstituted Furans through Palladium-Catalyzed Three-Component Condensation of Alkynylbenziodoxoles, Carboxylic Acids, and Imines |
title_full |
Modular Synthesis of Multisubstituted Furans through Palladium-Catalyzed Three-Component Condensation of Alkynylbenziodoxoles, Carboxylic Acids, and Imines |
title_fullStr |
Modular Synthesis of Multisubstituted Furans through Palladium-Catalyzed Three-Component Condensation of Alkynylbenziodoxoles, Carboxylic Acids, and Imines |
title_full_unstemmed |
Modular Synthesis of Multisubstituted Furans through Palladium-Catalyzed Three-Component Condensation of Alkynylbenziodoxoles, Carboxylic Acids, and Imines |
title_sort |
modular synthesis of multisubstituted furans through palladium-catalyzed three-component condensation of alkynylbenziodoxoles, carboxylic acids, and imines |
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2015 |
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https://hdl.handle.net/10356/103693 http://hdl.handle.net/10220/38788 |
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1759856557612335104 |