2013 Winner: In Situ Generation of Dichloroindium Hydride via Reduction of Indium (III) Chloride

Project Information
In Situ Generation of Dichloroindium Hydride via Reduction of Indium (III) Chloride
Physical and Biological Sciences
CHEM 195 Senior Thesis
Four alternative reduction systems for the in situ generation of HInCl2 were explored. Our goal was to investigate the reductive properties of HInCl2 generated in each system on nitriles, carbonyls, and halogens. Stoichiometric amounts of sodium borohydride (NaBH4), diisobutylaluminum hydride (DIBAL-H), or lithium dimethylaminoborohydride (MeLAB) were reacted with indium trichloride (InCl3) to generate HInCl2. Based on the method of generation and the solvent used (THF or CH3CN), HInCl2 was able to reduce 4-(halomethyl)benzonitriles selectively, partially, and tandemly to six distinct products with yields ranging from 60-99%. These reduction systems provide simple control of chemoselectivity, and are of great industrial significance to the total synthesis of therapeutic drugs.
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Students
  • Panathda Bayrasy (Nine)
Mentors