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General Methodology for the Preparation of Unsymmetrical α-Linked Bisenones via Ligandless Cross-Coupling Reactions

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    General Methodology for the Preparation of Unsymmetrical α-Linked Bisenones via Ligandless Cross-Coupling Reactions
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    Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, United States
    *E-mail: [email protected]
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    Organic Letters

    Cite this: Org. Lett. 2017, 19, 7, 1730–1733
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    https://doi.org/10.1021/acs.orglett.7b00497
    Published March 20, 2017
    Copyright © 2017 American Chemical Society
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    Abstract

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    A stereocontrolled Stille cross-coupling reaction, involving the use of Pd2dba3, provides a general procedure for the synthesis of unsymmetrical α-linked bisenone systems. The transformation is achieved in the absence of phosphine ligands under conditions that promote the stabilization of “ligandless” palladium catalysis. The extension of these studies illustrates Suzuki–Miyaura reactions of 2-boryl-2-cyclohexen-1-one with iodide and triflate partners for the synthesis of novel electron-deficient 1,3-dienes.

    Copyright © 2017 American Chemical Society

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    Organic Letters

    Cite this: Org. Lett. 2017, 19, 7, 1730–1733
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.7b00497
    Published March 20, 2017
    Copyright © 2017 American Chemical Society
    Request reuse permissions

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