The chemistry of heterocyclic compounds is used in almost all aspects of organic chemistry, medicinal chemistry, and biochemistry. Methods that can generate these compounds at milder conditions and lower costs are of utmost value. A 1,3-dipolar cycloaddition reaction is a common reaction to synthesize heterocyclic compounds. The current method for this reaction requires reacting a diazo compound with a rhodium catalyst. Rhodium is one of the most expensive and least abundant metals used for catalysis. Ruthenium is a cheaper solution that can be utilized. The goal of this project is to synthesize diazo compounds (1) that can be reacted with two different ruthenium catalysts (3 & 4) in order to produce a ruthenacarbene intermediate (2) which can then react with a dipolaraphile (DMAD)(7) to generate a heterocycle (5). The two catalysts that will be screened are the Grubbs Generation-I catalyst (3) and the tris(triphenylphosphine)ruthenium(II)dichloride catalyst (4). The optimal conditions at which these two catalysts generate the ruthenacarbene intermediate will also be determined. Not only does this reaction provide a more economical process for the synthesis of heterocycles, it also has the potential to impact the discovery of pharmaceutical drugs, insectisides, and various other chemicals.

1,3-Dipolar cycloaddition reaction

249th National Meeting (2015)

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