title: Palladium(II)-Catalyzed Synthesis of Sulfinates from Boronic Acids and DABSO: A Redox-Neutral, Phosphine-Free Transformation.
abstract: A redox-neutral palladium(II)-catalyzed conversion of aryl, heteroaryl, and alkenyl boronic acids into sulfinate intermediates, and onwards to sulfones and sulfonamides, has been realized. A simple Pd(OAc)2 catalyst, in combination with the sulfur dioxide surrogate 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO), is sufficient to achieve rapid and high-yielding conversion of the boronic acids into the corresponding sulfinates. Addition of C- or N-based electrophiles then allows conversion into sulfones and sulfonamides, respectively, in a one-pot, two-step process.
authors.affiliation: 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.forename: Alex S
authors.initials: AS
authors.lastname: Deeming
authors.affiliation: Syngenta, Jealott's Hill International Research Centre, Bracknell, Berkshire, RG42 6EY (UK).
authors.forename: Claire J
authors.initials: CJ
authors.lastname: Russell
authors.affiliation: Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA (UK) http://mcwillis.chem.ox.ac.uk/MCW/Home.html. michael.willis@chem.ox.ac.uk.
authors.forename: Michael C
authors.initials: MC
authors.lastname: Willis
keywords: electrophiles; oxidation; palladium; sulfur; synthetic methods