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Issue 20, 2012
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Palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides: scope of the three-component synthesis of N-aminosulfonamides

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Abstract

By using DABCO·(SO2)2, DABSO, as a solid bench-stable SO2-equivalent, the palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides has been achieved. N,N-Dialkylhydrazines are employed as the N-nucleophiles and provide N-aminosulfonamides as the products in good to excellent yields. The reactions are operationally simple to perform, requiring only a slight excess of SO2 (1.2–2.2 equiv.), and tolerate a variety of substituents on the halide coupling partner. Variation of the hydrazine component is also demonstrated. The use of N,N-dibenzylhydrazine as the N-nucleophile delivers N-aminosulfonamide products that can be converted into the corresponding primary sulfonamides using a high-yielding, telescoped, deprotection sequence. The ability to employ hydrazine·SO2 complexes as both the N-nucleophile and SO2 source is also illustrated.

Graphical abstract: Palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides: scope of the three-component synthesis of N-aminosulfonamides

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Publication details

The article was received on 05 Dec 2011, accepted on 10 Feb 2012 and first published on 13 Feb 2012


Article type: Paper
DOI: 10.1039/C2OB07034K
Citation: Org. Biomol. Chem., 2012,10, 4007-4014
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    Palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides: scope of the three-component synthesis of N-aminosulfonamides

    E. J. Emmett, C. S. Richards-Taylor, B. Nguyen, A. Garcia-Rubia, B. R. Hayter and M. C. Willis, Org. Biomol. Chem., 2012, 10, 4007
    DOI: 10.1039/C2OB07034K

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