title: One-Pot Sulfoxide Synthesis Exploiting a Sulfinyl-Dication Equivalent Generated from a DABSO/Trimethylsilyl Chloride Sequence.
abstract: A one-pot process for the synthesis of unsymmetrical sulfoxides using organometallic nucleophiles is described. Sulfur dioxide, delivered from the surrogate DABSO (DABCO-bis(sulfur dioxide)), acts as the initial electrophile and combines with the first organometallic reagent to generate a sulfinate intermediate. In situ conversion of the sulfinate to a sulfinate silyl ester, using TMS-Cl (trimethylsilyl chloride), generates a second electrophile, allowing addition of a second organometallic reagent. Organolithium or Grignard reagents can be employed, delivering sulfoxides in good to excellent yields.
authors.affiliation: Department of Chemistry, University of Oxford , Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, United Kingdom.
authors.forename: Danny C
authors.initials: DC
authors.lastname: Lenstra
authors.affiliation: Department of Chemistry, University of Oxford , Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, United Kingdom.
authors.forename: Vincent
authors.initials: V
authors.lastname: Vedovato
authors.affiliation: Department of Chemistry, University of Oxford , Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, United Kingdom.
authors.forename: Emmanuel
authors.initials: E
authors.lastname: Ferrer Flegeau
authors.affiliation: Department of Chemistry, University of Oxford , Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, United Kingdom.
authors.forename: Jonathan
authors.initials: J
authors.lastname: Maydom
authors.affiliation: Department of Chemistry, University of Oxford , Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, United Kingdom.
authors.forename: Michael C
authors.initials: MC
authors.lastname: Willis