Sulfonyl Azides as Precursors in Ligand-free Palladium-Catalyzed Synthesis of Sulfonyl Carbamates and Sulfonyl Ureas and Synthesis of Sulfonamides
2016 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 81, no 7, 2681-2691 p.Article in journal (Refereed) Published
An efficient synthesis of sulfonyl carbamates and sulfonyl ureas from sulfonyl azides employing a palladium-catalyzed carbonylation protocol has been developed. Using a two-chamber system, sulfonyl azides, PdCl2, and CO gas, released ex situ from Mo(CO)(6), were assembled to generate sulfonyl isocyanates in situ, and alcohols and aryl amines were exploited as nucleophiles to afford a broad range of sulfonyl carbamates and sulfonyl ureas. A protocol for the direct formation of substituted sulfonamides from sulfonyl azides and amines via nucleophilic substitution was also developed.
Place, publisher, year, edition, pages
2016. Vol. 81, no 7, 2681-2691 p.
Research subject Chemistry with specialization in Organic Chemistry
IdentifiersURN: urn:nbn:se:uu:diva-281023DOI: 10.1021/acs.joc.5b02755ISI: 000373520200001PubMedID: 26967791OAI: oai:DiVA.org:uu-281023DiVA: diva2:912552
FunderKnut and Alice Wallenberg FoundationCarl Tryggers foundation