C-H Bond Functionalization

C-H Bond Functionalization

Our group has discovered some of the most widely practiced C-H bond functionalization reactions. We discovered that metal boryl compounds react with arenes and alkanes to form functionalized products and developed this new elementary reaction into a catalytic process for the conversion of alkyl and aryl C-H bonds into C-B bonds. The C-B bonds in the product can then be converted to C-C and C-heteroatom bonds in a wide range of valuable products. We have also recently extended this type of catalysis to the formation of C-Si bonds from silane reagents. We are now seeking to apply this chemistry to the functionalization complex arenes and heteroarenes and to the discovery of catalysts that functionalize aliphatic C-H bonds in molecules with complex structures and with a range of auxiliary functionality.

Our success on the functionalization of C-H bonds in complex molecules with boranes and silanes has led us to develop additional classes of C-H bond functionalizations. For example, we recently disclosed a combination of catalyst and reagent for the conversion of C-H bonds in natural products to the C-N bonds in alkyl azides. Reduction of the azide leads to natural product analogs containing amino groups, as well as related nitrogen-based functionality.