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

Dirk H. Ortgies; Alexandre Barthelme; Sara Aly; Brigitte Desharnais; Steven Rioux; Pat Forgione

doi:10.1055/s-0032-1318151

Synthesis, Table of Contents

Synthesis 2013; 45(5): 694-702
DOI: 10.1055/s-0032-1318151

paper

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

,

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

,

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

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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.

Key words

palladium - sulfur - cross-coupling - catalysis - biaryls

Full Text

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