An Improved Suzuki-Miyaura Cross-Coupling Reaction for the Synthesis of Fluorine-Substituted 3-Biaryl-1-ferrocenyl-2-propen-1-one

Abstract

We studied the Pd(0)-catalyzed Suzuki-Miyaura cross-coupling reaction and obtained an improved procedure with shorter reaction times and higher conversions.

We investigated two methods stepwise addition of reagents and addition of all the reagents at the same time. We found that the reaction rate of the former is faster than the latter. Methanol was shown to be the optimum solvent for the reaction, however with an alcohol as the solvent the reaction was complete in under 1.5 hours. This improved methodology was applied to the synthesis of novel fluorine-substituted 3-biaryl-1-ferrocene-propene-1-ones, which were synthesized in good yields.

Keywords

Suzuki cross-coupling reaction - Pd(0) catalyst - alcohol solvents - ferrocene derivatives - biaryl

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