Summer Undergraduate Research Mentored Experience

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Dr. Katja Michael

Department of Chemistry

Photochemical synthesis of organic compounds – a method development project

Preferred major field of study or minimum required skills

chemistry major, basic organic chemistry skills in theory and practice

Scholarly significance/intellectual merit

as the non-methylated parent compound?In synthetic organic chemistry, most of the already existing photoreactive compounds are used as protecting groups that can be cleaved with UV light to liberate alcohols, carboxylic acids, and amines. Unlike ordinary photoreactive protecting groups, N-acyl-nitroindolines are a special group of photoreactive compounds that are capable of an acyl transfer to a variety of nucleophiles, such as amines, aminals, hydrazine, alcohols, and thiols (see for example two publications from our research group: Kaneshiro & Michael, Angew. Chem. Int. Ed. 2006, 45, 1077; and Pardo et al., ChemBioChem 2015, 16, 1884). These photochemical acylation reactions produce amides, oxoesters, thioesters, and hydrazides under mild conditions, and are therefore very useful synthetic tool. There are a number of nucleophiles that have never been explored in this acyl transfer photochemistry, e.g. organometallic reagents, enolates, and azides. Based on the published photolysis mechanism of N-acyl-nitroindolines (Morrison et al., Photochem. Photobiol. Sci. 2002, 1, 960) we expect that the illumination of N-acylnitroindolines in the presence of these nucleophiles can produce aldehydes, ketones, acylazides, and dicarbonyl compounds.

Research question(s)

  • Can photochemistry be used to produce aldehydes, ketones, acylazides, and dicarbonyl compounds from N-acyl-nitroindolines with organometallic reagents, azides, and enolates?
  • What are the best solvents for these reactions?
  • Are any catalysts or auxiliary nucleophiles, such as N-hydroxybenzotriazole or N-hydroxysuccinimide, required?
  • Do these reactions result in significant amounts of undesired by-products?
  • What kind of acyl residues on the N-acyl-nitroindolines are suitable?

Methods/techniques/instruments to be learned/utilized

The undergraduate student will receive training in the laboratory techniques required for the synthesis of small organic molecules, in synthetic photochemistry, in compound purification by chromatography, and in compound analysis by mass spectrometry, infrared spectroscopy, and 1H and 13C nuclear magnetic resonance spectroscopy.