%0 Generic
%9 Doctoral Dissertation
%A Nerkar, Swapnil
%D 2017
%F pittir:33053
%K NHC-Boranes, Suzuki Coupling
%T Synthesis and Reactions of Alkyl- and Aryl-Substituted N-Heterocyclic Carbene Boranes
%U http://d-scholarship-dev.library.pitt.edu/33053/
%X Synthesis and applications of alkyl- and aryl-substituted NHC-boranes has been demonstrated. Chapter 1 shows the synthesis of methyl- and phenyl-substituted NHC-boranes by using organolithium reagents. Other alkyl- and aryl-substituted NHC-boranes have been prepared by hydroboration of alkenes and arynes respectively. The prepared substituted NHC-boranes were converted to Suzuki coupling precursors such as boronic acids, trifluoroborate salts, pinacol boronate esters and MIDA boronates. Fluorinated NHC-boranes were made by electrophilic fluorination of NHC-boranes with Selectfluor. The diMe-Imd-BF2H has been synthesized via the use of a nucleophilic fluorination source (TBAF). The corresponding boryl radical has been generated and its properties have been compared to the boryl radical of the parent diMe-Imd-BH3.  Chapter 2 describes the use of B-halo substituted NHC-boranes in the Suzuki coupling reactions. The NHC-(dibromo)arylboranes are converted to the boronic acids in-situ while the NHC-(difluoro)arylboranes are analogous to potassium trifluoroborate salts and used directly in the Suzuki coupling reaction. The potential for the use of NHC-(difluoro)arylboranes as a boron masking partner has been demonstrated. NHC-(difluoro)pinylborane has been used in the Minisci reaction showcasing the utility of NHC-boranes as a new boron partner in the C-C bond formation reactions.