On the Amine-Catalyzed Suzuki-Miyaura Coupling Using a Catalysis-Based Fluorometric Method

16 April 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The Suzuki-Miyaura coupling is one of the most frequently used reactions in organic synthesis. Recent work by others suggested that an arylamine, prepared by palladium catalysis, could catalyze Suzuki-Miyaura coupling reactions without transition metals. Herein, we used a fluorometric quantification method for palladium previously developed in our laboratory to unambiguously conclude that there is a correlation between the palladium content in the arylamine and the rate of a Suzuki-Miyaura coupling. Also, our mass spectroscopic analysis of the arylamine revealed the presence of a palladium-phosphine complex. We discovered that the phosphine was detrimental to the palladium catalysis and that the arylamine played negligible role. This study demonstrates the utility of the fluorometric technology for catalysis research.

Keywords

palladium
fluorescence assay
Suzuki-Miyaura
Amine
phosphine

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