Two broad areas of investigation are proposed. The first concentrates on the chemistry of samarium(ll) iodide and in particular its unique ability to mediate sequential processes that selectively transform simple starting materials to interesting products with considerable increase in molecular complexity. Unlike previous efforts in our group, we will devote substantial effort to the assembly of nitrogen heterocycles via synthetic pathways unique to this valuable reagent. Sequenced reactions to be explored include a conjugate addition/nucleophilic acyl substitution sequence, ketyl allene coupling/radical sequences, and sequences initiated by N-centered radicals. ? ? The second area of consideration is the application of organotrifluoroborates to organic synthesis. We have spent some time outlining the ways in which these useful reagents complement more commonly utilized classes of organoboron compounds in Suzuki-Miyaura cross-coupling reactions and certainly considerable advantages exist. In this proposal, however, we focus on the types of transformations that, for structural reasons, simply cannot be carried out with any other organoboron reagents. These include the synthesis of bimetallic reagents in which one of the metal centers is boron, and the development of unique reagents in which organic functionality has been oxidized in the presence of the trifluoroborate moiety. ? ? These types of transformations are anticipated to have broad generality and will thus prove valuable for the rapid, efficient, and unique assembly of complex organic molecules throughout the pharmaceutical industry and beyond. ? ?
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