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Improved Synthesis of Functionalized 2,2‘-Bipyrroles

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    Improved Synthesis of Functionalized 2,2‘-Bipyrroles
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    Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803 [email protected]
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2007, 72, 21, 8119–8122
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    https://doi.org/10.1021/jo701310k
    Published September 21, 2007
    Copyright © 2007 American Chemical Society
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    Abstract

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    A series of 2,2‘-bipyrroles has been efficiently synthesized using an improved synthetic approach based on Pd(0)-catalyzed homocoupling of various 2-iodopyrroles. This new synthetic approach takes place at room temperature and in the presence of water. Functional groups such as formyl, ester, and nitrile are able to survive these reaction conditions. Solvents are found to play an important role in this reaction.

    Copyright © 2007 American Chemical Society

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    Supporting Information Available

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    Synthetic procedures for compounds 6a−d, 4a−d, and dibenzyl 3,3‘,4,4‘-tetramethyl-2,2‘-bipyrrole-5,5‘-dicarboxylate, spectroscopic characterization and 1H NMR/13C NMR spectra of compounds 1a−e, 6a−d, 4a−d, and dibenzyl 3,3‘,4,4‘-tetramethyl-2,2‘-bipyrrole-5,5‘-dicarboxylate; ESI HRMS spectra for compounds 1a−e, 4c, 4d, and dibenzyl 3,3‘,4,4‘-tetramethyl-2,2‘-bipyrrole-5,5‘-dicarboxylate. This material is available free of charge via the Internet at http://pubs.acs.org.

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    This article is cited by 36 publications.

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    36. Lijuan Jiao, Erhong Hao, M. Graca H. Vicente, Kevin M. Smith. ChemInform Abstract: Improved Synthesis of Functionalized 2,2′‐Bipyrroles.. ChemInform 2008, 39 (7) https://doi.org/10.1002/chin.200807102
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2007, 72, 21, 8119–8122
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo701310k
    Published September 21, 2007
    Copyright © 2007 American Chemical Society
    Request reuse permissions

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