“Our greatest glory consists not in never failing, but rising up every time we fail” Ralph Waldo Emerson
Hilary graduated from the University of Delaware with her B.S. in chemistry and a minor in psychology in May 2013. Throughout her undergraduate studies she worked with Prof. Mary Watson on the enantioselective addition of carbon nucleophiles to oxocarbenium ion intermediates, earning her both a GSK Summer Fellowship and an ACS-Organic Division Summer Undergraduate Research Fellowship. Hilary is currently a rising fourth year in the Montgomery lab at the University of Michigan. Her work consists of hydroborations of unactivated olefins.
Advances in Regioselective Borylations of Pi Systems
Suzuki-Miyarua cross couplings are among the most important and versatile methods for the synthesis of pharmaceuticals and potential drug candidates. Classical hydroboration methods of terminal alkenes select for the synthesis of primary alkyl boranes. Reversal of this well known method enables synthesis of secondary alkyl boranes from simple alkene precursors that diversifies and changes the perspective of hydroboration reactions. A method for regioselective hydroboration of terminal alkenes has been established to synthesize secondary branched alkyl boranes. The use of a bulky copper-N-heterocyclic carbene (NHC) in the presence of a diboron reagent and methanol affords the branched alkyl borane in high regiocontrol. This methodology shows a wide variety of chemoselectivity, tolerating protected alcohols, aryl bromides, and allyl heterocycles. Furthermore, the newly synthesized alkyl boranes successfully undergo cross-coupling reactions with aryl halides. Current efforts are focused on advances in regioselective hydroboration of unactivated, internal olefins and in the trifunctionalization of allenes.