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

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
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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
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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
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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
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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
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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
› Author Affiliations
Further Information

Publication History

Received: 20 November 2012

Accepted after revision: 10 January 2013

Publication Date:
04 February 2013 (online)


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