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An experiment featuring an operationally simple Suzuki–Miyaura cross-coupling reaction suitable for a second-semester, second-year undergraduate organic chemistry laboratory course is presented. The cross-coupling reaction between 4-bromobenzoic acid and phenylboronic acid is run entirely in water and features an easily prepared and affordable palladium catalyst that requires no specialized equipment as the reaction can be run in a flask or beaker that is open to air. The product precipitates directly from the reaction mixture and is purified by a straightforward recrystallization from aqueous hydrochloric acid and ethanol. The cross-coupling reaction requires only 30 min of reaction time, allowing ample time to coordinate this reaction with other instructive exercises, such as recrystallization, melting point determination, and IR and NMR spectroscopy. The solvents used in the synthesis and purification provide a link to the growing commitment to sustainable chemistry in teaching laboratories and how safe, renewable solvents and catalysis play a role in green chemistry.

Development of a sensor capable of selective detection of specific nerve agents is imperative in today's atmosphere of terrorism. The sensor needs to be inexpensive, portable, reliable, absent of false positives and available to all military and first responders. By utilizing the techniques of molecular imprinting, combinatorial chemistry, silica sol-gel synthesis and lanthanide luminescence, a sensor for the detection of the hydrolysis product of the nerve agent soman is being developed. There are many parameters that require investigation in order for the sensor to become a reality. These parameters include 1) the selection of a chelate that can bind to the lanthanide and anchor the nerve agent simulant during the formation of the molecularly imprinted polymer, 2) the determination of the environment best suited for this complex formation, 3) the formation, as well as modification of the silica sol-gel for molecular imprinting to take place, and 4) the proper quantity and ratios of monomers used to create the three dimensional imprint. Key to the success of optimizing these parameters is the development of a combinatorial assay that allows for the synthesis and testing of tens of thousands of combinations of parameters. Work on the development of the combinatorial assay has lead to a method of preparing thin film polymers capable of analyzing the presence of nerve agent simulants. Current work is underway to validate the combinatorial assay and to synthesize and evaluate a library of sensor materials selective for nerve agents.

A tandem SN2‐Michael addition reaction has been developed for the synthesis of cis‐ and trans‐fused nitrogen and sulfur heterocycles from the cis and trans isomers of ethyl (±)‐(2E)‐3‐[2‐(iodomethyl)cyclo‐hexyl]‐2‐propenoate. Octahydro‐1H‐isoindole‐1‐acetic acid and octahydrobenzo[c]thiophene‐1‐acetic acid derivatives have been prepared and their stereochemistries elucidated using NMR and X‐ray crystallo‐graphic methods. Cyclization substrates for both the cis‐ and the trans‐fused rings are readily available in four steps from known compounds. Yields for the cyclization range from 80‐85% and stereochemical selec‐tivities with respect to the side chain vary from 12.5‐16:1 for the cis‐fused structures to 6‐7.5:1 for the trans‐fused structures. Steric interactions in the transition states for ring closure are proposed to rationalize the observed preferences.

The title compound, 1-(4-triethoxysilyl)phenyl)-4,4,4-trifluoro-1,3-butanedione, was synthesized in a three-step sequence starting from 2-(4-bromophenyl)propene. Containing both a trialkoxysilyl and a substituted 1,3-butanedione functional grouping within its structure, this new silane is a viable starting material for the preparation of functionalized sol-gel materials.