title: Palladium-catalyzed synthesis of ammonium sulfinates from aryl halides and a sulfur dioxide surrogate: a gas- and reductant-free process.
abstract: Sulfonyl-derived functional groups populate a broad range of useful molecules and materials, and despite a variety of preparative methods being available, processes which introduce the most basic sulfonyl building block, sulfur dioxide, using catalytic methods, are rare. Described herein is a simple reaction system consisting of the sulfur dioxide surrogate DABSO, triethylamine, and a palladium(0) catalyst for effective convertion of a broad range of aryl and heteroaryl halides into the corresponding ammonium sulfinates. Key features of this gas- and reductant-free reaction include the low loadings of palladium (1 mol%) and ligand (1.5 mol%) which can be employed, and the use of isopropyl alcohol as both a solvent and formal reductant. The ammonium sulfinate products are converted in situ into a variety of sulfonyl-containing functional groups, including sulfones, sulfonyl chlorides, and sulfonamides.
authors: Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA (UK) http://mcwillis.chem.ox.ac.uk/MCW/Home.html.
authors: Edward J
authors: EJ
authors: Emmett
authors: Barry R
authors: BR
authors: Hayter
authors: Michael C
authors: MC
authors: Willis
mesh_terms: D002384:Catalysis; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013441:Sulfinic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013458:Sulfur Dioxide / Q000737:chemistry*
chemical_list: D006846:Hydrocarbons, Halogenated; D009942:Organometallic Compounds; D000644:Quaternary Ammonium Compounds; D013441:Sulfinic Acids; D013458:Sulfur Dioxide; D010165:Palladium
keywords: alcohols; arenes; palladium; sulfonamides; synthetic methods