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Gold(I)-Catalyzed Cross-Coupling Reactions of Arenediazonium Salts with Alkynoic Acids

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Abstract

The reaction of simple alkynoate salts with isolated arenediazonium tetrafluoroborate salts that had been pre-conditioned with the gold(I) catalyst AuCl(Me2S) led to the formation of cross-coupled products via a decarboxylative Sonogashira reaction process in modest yield and under mild conditions. The major by-product is a defunctionalized aryl moiety stemming from the diazonium salt, which competitively forms via hydrodediazonation. Good functional group tolerance and reaction site selectivity were attained in this limited investigation.

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ACKNOWLEDGMENTS

The authors thank Dr. Y. Rezenom, Director of the mass spectrometry facilities at Texas A&M University College Station, who generously analyzed several of our samples. We thank the following for NMR spectral analysis of our compounds: Dr. G. Wylie, NMR Instrument Facility Manager at Texas A&M University College Station and Dr. I. Ghiviriga, NMR Specialist and Research Faculty in the Department of Chemistry at University of Florida. We also thank the following for providing NMR instrument access: Dr. N. Kraiouchkine, Department of Chemistry Instrument Coordinator at Texas A&M University–Corpus Christi and Dr. S. Sitaula, Chemistry Professor at Texas A&M International University Laredo.

Funding

This work was supported by a Welch Foundation Grant (AC-0006) to the Department of Chemistry at Texas A&M University–Kingsville.

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  1. Department of Chemistry, Texas A&M University–Kingsville, 78363, Kingsville, Texas, USA

    J. N. Abrams & B. K. Chi

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Abrams, J.N., Chi, B.K. Gold(I)-Catalyzed Cross-Coupling Reactions of Arenediazonium Salts with Alkynoic Acids. Russ J Org Chem 56, 1236–1244 (2020). https://doi.org/10.1134/S1070428020070180

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