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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Main Authors:	Wu, Junliang, Yoshikai, Naohiko
其他作者:	School of Physical and Mathematical Sciences
格式:	Article
語言:	English
出版:	2015
主題:	DRNTU::Science::Chemistry
在線閱讀:	https://hdl.handle.net/10356/103693 http://hdl.handle.net/10220/38788
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spelling	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
institution	Nanyang Technological University
building	NTU Library
continent	Asia
country	Singapore Singapore
content_provider	NTU Library
collection	DR-NTU
language	English
topic	DRNTU::Science::Chemistry
spellingShingle	DRNTU::Science::Chemistry Wu, Junliang Yoshikai, Naohiko Modular Synthesis of Multisubstituted Furans through Palladium-Catalyzed Three-Component Condensation of Alkynylbenziodoxoles, Carboxylic Acids, and Imines
description	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.
author2	School of Physical and Mathematical Sciences
author_facet	School of Physical and Mathematical Sciences Wu, Junliang Yoshikai, Naohiko
format	Article
author	Wu, Junliang Yoshikai, Naohiko
author_sort	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
publishDate	2015
url	https://hdl.handle.net/10356/103693 http://hdl.handle.net/10220/38788
_version_	1759856557612335104

Modular Synthesis of Multisubstituted Furans through Palladium-Catalyzed Three-Component Condensation of Alkynylbenziodoxoles, Carboxylic Acids, and Imines

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