Aryl-core compounds are found in many pharmaceutical products, making the efficient synthesis of these compounds increasingly important in organic chemistry. The Suzuki-Miyaura cross-coupling reaction (SMC) is often used to synthesize these products, owing to numerous commercially available reagents, mild reaction conditions, and tolerance to diverse functional groups. Methods to rapidly generate diverse furan compounds through the SMC is of interest to the medicinal chemistry community as these compounds comprise the core structure of numerous pharmaceuticals and natural products. The focus of this research involves the development of a one-pot SMC coupling process that uses di-brominated furans to produce differentially tri-substituted furan products in one synthetic operation. Optimization of this sequence included examination of different solvents, palladium catalysts, and reaction times in addition to altering the amounts of the catalyst and bases used. We found the optimized conditions desired for bis-coupling used Pd(OAc)<sub>2 </sub>as catalyst, sodium carbonate as base, and 1:1 water/dimethylformamide (DMF) solution as solvent at 75 °C. Starting from di-brominated furans substituted with ether, aldehyde, or amide functional groups, differentially tri-substituted furans have successfully been generated via the one-pot procedure in yields ranging from 50-88%. Future work includes modifications of the reaction conditions to further improve yield and assessing the effect of different functional groups on reaction yields.

Synthesis of tri-substituted furans via sequential one-pot suzuki-miyaura coupling reactions

ACS Spring 2022

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