Cross-coupling reactions are extremely useful in creating carbon-carbon and carbon-heteroatom bonds in pharmaceutical, agricultural, and industrial chemistry. In particular, the Suzuki cross-coupling reaction involves a boronic ester, which contains a critical carbon-boron bond that is useful for forming carbon-carbon bonds after catalysis. Existing methods to prepare these substrates have serious limitations. Our research aims to make carbon-boron bonds under more generally useful borylation conditions by using easily synthesized aryl sulfamates and a cost effective nickel catalyst. Current research is focused on exploring the substrate scope and optimizing isolation. Substrates with various electronic and structural properties were tested for successful borylation. Additionally, purification of the product was refined through adjustments in isolation conditions and incorporation of oxidizing stains. Aryl sulfamate substrates containing electron-withdrawing groups were found to be favorable for borylation, producing higher yields. Isolation proved more effective with the use of a slightly basic adsorbent and potassium permanganate staining to identify suitable chromatography conditions. Future directions include continuing to explore the substrate scope, refine isolation procedures, and characterize isolated products.

Nickel-catalyzed borylation of aryl sulfamates

2019 Spring National Meeting

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.