Literature DB >> 26230623

Modular synthesis of multisubstituted furans through palladium-catalyzed three-component condensation of alkynylbenziodoxoles, carboxylic acids, and imines.

Junliang Wu1, Naohiko Yoshikai2.   

Abstract

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.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  furans; hypervalent iodine compounds; imines; multicomponent reactions; palladium

Mesh:

Substances:

Year:  2015        PMID: 26230623     DOI: 10.1002/anie.201504687

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  5 in total

1.  Light-Driven Intermolecular Charge Transfer Induced Reactivity of Ethynylbenziodoxol(on)e and Phenols.

Authors:  Bin Liu; Chern-Hooi Lim; Garret M Miyake
Journal:  J Am Chem Soc       Date:  2018-10-02       Impact factor: 15.419

2.  Unconventional Reactivity of Ethynylbenziodoxolone Reagents and Thiols: Scope and Mechanism.

Authors:  Bin Liu; Juan V Alegre-Requena; Robert S Paton; Garret M Miyake
Journal:  Chemistry       Date:  2020-01-22       Impact factor: 5.236

3.  Diastereoselective Synthesis of Cyclopenta[c]furans by a Catalytic Multicomponent Reaction.

Authors:  Stalin R Pathipati; Angela van der Werf; Lars Eriksson; Nicklas Selander
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-19       Impact factor: 15.336

4.  Cys-Cys and Cys-Lys Stapling of Unprotected Peptides Enabled by Hypervalent Iodine Reagents.

Authors:  Javier Ceballos; Elija Grinhagena; Gontran Sangouard; Christian Heinis; Jerome Waser
Journal:  Angew Chem Int Ed Engl       Date:  2021-03-08       Impact factor: 15.336

5.  Multicomponent formation route to a new class of oxygen-based 1,3-dipoles and the modular synthesis of furans.

Authors:  Huseyin Erguven; Cuihan Zhou; Bruce A Arndtsen
Journal:  Chem Sci       Date:  2021-10-27       Impact factor: 9.825

  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.