Synthesis 2013; 45(5): 694-702
DOI: 10.1055/s-0032-1318151
paper
© Georg Thieme Verlag Stuttgart · New York

Scope of the Desulfinylative Palladium-Catalyzed Cross-Coupling of Aryl Sulfinates with Aryl Bromides

Authors

  • Dirk H. Ortgies

    Concordia University, Department of Chemistry and Biochemistry, 7141 rue Sherbrooke O., Montréal, QC, H4B 1R6, Canada and Centre for Green Chemistry and Catalysis, CP 6128, succursale Centre-ville, Montréal, QC, H3C 3J7, Canada   Fax: +1(514)8482868   Email: pat.forgione@concordia.ca
  • Alexandre Barthelme

    Concordia University, Department of Chemistry and Biochemistry, 7141 rue Sherbrooke O., Montréal, QC, H4B 1R6, Canada and Centre for Green Chemistry and Catalysis, CP 6128, succursale Centre-ville, Montréal, QC, H3C 3J7, Canada   Fax: +1(514)8482868   Email: pat.forgione@concordia.ca
  • Sara Aly

    Concordia University, Department of Chemistry and Biochemistry, 7141 rue Sherbrooke O., Montréal, QC, H4B 1R6, Canada and Centre for Green Chemistry and Catalysis, CP 6128, succursale Centre-ville, Montréal, QC, H3C 3J7, Canada   Fax: +1(514)8482868   Email: pat.forgione@concordia.ca
  • Brigitte Desharnais

    Concordia University, Department of Chemistry and Biochemistry, 7141 rue Sherbrooke O., Montréal, QC, H4B 1R6, Canada and Centre for Green Chemistry and Catalysis, CP 6128, succursale Centre-ville, Montréal, QC, H3C 3J7, Canada   Fax: +1(514)8482868   Email: pat.forgione@concordia.ca
  • Steven Rioux

    Concordia University, Department of Chemistry and Biochemistry, 7141 rue Sherbrooke O., Montréal, QC, H4B 1R6, Canada and Centre for Green Chemistry and Catalysis, CP 6128, succursale Centre-ville, Montréal, QC, H3C 3J7, Canada   Fax: +1(514)8482868   Email: pat.forgione@concordia.ca
  • Pat Forgione*

    Concordia University, Department of Chemistry and Biochemistry, 7141 rue Sherbrooke O., Montréal, QC, H4B 1R6, Canada and Centre for Green Chemistry and Catalysis, CP 6128, succursale Centre-ville, Montréal, QC, H3C 3J7, Canada   Fax: +1(514)8482868   Email: pat.forgione@concordia.ca
Further Information

Publication History

Received: 20 November 2012

Accepted after revision: 10 January 2013

Publication Date:
04 February 2013 (online)


Graphical Abstract

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Dedicated to the memory of Keith Fagnou

Abstract

Herein is described the full scope of a desulfinylative cross-coupling of aryl sulfinates with aryl bromides. Optimized conditions were established and a bidentate phosphine ligand was found to be the key in obtaining good cross-coupling yields. Preliminary efforts to elucidate the reaction mechanism suggest that a Pd(0)-catalyzed mechanism is operative.

Supporting Information