Chemoselective reduction is an important tool in synthetic organic chemistry.  Selective, tandem, and partial reductions are important for compounds that contain two or more functional groups. Development of partial, selective, and tandem reaction cascades can help reduce or eliminate the use of protecting groups in total synthesis.  There are many metal hydrides available, however HInCl2 is particularly interesting because of its mild reducing properties, which enable it to efficiently and selectively reduce a variety of different functional groups.  It is also useful because there are multiple ways to generate dichloroindium hydride.  The reductive capability of InCl3/NaBH4 system has been found to be highly dependent on the solvent used. Investigation by 11B NMR spectroscopic indicates the reaction of InCl3 and NaBH4 in THF generates HInCl2 along with BH3:THF in situ.  Alkyl halide and nitrile or carbonyl functional groups were reduced in tandem by utilizing the reductive capabilities of both HInCl2 and BH3:THF in a one-pot reaction. Selective reduction of the carbon-bromine bond in the presence of nitrile or carbonyl functionalities has been achieved by generating HInCl2 via the reduction InCl3 with NaBH4 in acetonitrile.  Carefully controlling the activity of these reducing agents allows for the tandem, selective, and/or partial reduction of multi-functionalized compounds containing nitriles, halogens, and a variety of carbonyls.

Synthesis of dichloroindium hydride and its utility as a mixed metal hydride

248th National Meeting (2014)

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