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. 2020 May 4;59(19):7372-7376.
doi: 10.1002/anie.201915425. Epub 2020 Mar 17.

Sulfur(IV)-Mediated Unsymmetrical Heterocycle Cross-Couplings

Min Zhou  1 , Jet Tsien  1 , Tian Qin  1
Affiliations

Sulfur(IV)-Mediated Unsymmetrical Heterocycle Cross-Couplings

Min Zhou et al. Angew Chem Int Ed Engl. .

Erratum in

Abstract

Despite the tremendous utilities of metal-mediated cross-couplings in modern organic chemistry, coupling reactions involving nitrogenous heteroarenes remain a challenging undertaking - coordination of Lewis basic atoms into metal centers often necessitate elevated temperature, high catalyst loading, etc. Herein, we report a sulfur (IV) mediated cross-coupling amendable for the efficient synthesis of heteroaromatic substrates. Addition of heteroaryl nucleophiles to a simple, readily-accessible alkyl sulfinyl (IV) chloride allows formation of a trigonal bipyramidal sulfurane intermediate. Reductive elimination therefrom provides bis-heteroaryl products in a practical and efficient fashion.

Keywords: cross-coupling; heterocycles; sulfur; sulfurane.

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References

    1. None
    1. Trends in Cross-Coupling: Theory and Applications (Ed.: T. Colacot), The Royal Society of Chemistry, London, 2015;
    1. Science of Synthesis: Cross Coupling and Heck-Type Reactions, Workbenh Edition (Eds: G. Molander, J. P. Wolfe, M. Larhed), Thieme, Stuttgart, 2013.
    1. J. F. Hartwig, Organotransition metal chemistry-from bonding to catalyst, University Science Books, Sausalito, 2010, Chapter 8.
    1. For reviews on metal-catalyst cross-couplings, see:

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