"C-H bonds are pervasive in organic compounds, and methods for their functionalization are of particular interest. One method for functionalizing C-H bonds is through iridium catalyzed C-H borylation. The transformation of C-H bonds to C-B bonds opens up many synthetic routes, because of the versatility of the C-B bond. In the first section, iridium-catalyzed deborylation is used to selectively deuterate aromatic substrates. This method is highly selective as deuterium is only incorporated where the Bpin had previously resided. It is also milder as it does not use harsher acidic conditions, which makes it more applicable to substatrates that may be sensitive to those conditions. The next sections discuss methods for selective C-H borylations of enamines and phenols. The selective borylation reaction of enamines directed by a hydrogen-bonding interaction between the NH of the enamine and O of a boryl is discussed. This method allows of the selective C-H borylation of trans alkene C-H bonds with no borylation observed on the arene for styryl substrates. Then, the traceless protection of phenols by HBpin for C-H borylation is discussed. The protection of the phenols by HBpin leads to electrostatic interactions between the bipyridine ligand of an iridium catalyst and the O-Bglycolate to direct the ortho-borylation. In cases where Bpin is used as the protecting group, phenols with a substituent in the 4-position larger than fluorine generally had >99:1 ortho-selectivity. For phenols with substitution in the 2- or 3-positions or fluorine in the 4-position, Beg was used to increase stability of the transition states and therefore, the ortho-selectivity. In the final section C-H borylation is used to functionalize 1,10-phenanthroline for to provide simple, high yielding routes to functionalized ligands using the versatility of the C-B bond."--Pages ii-iii.
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