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SUMMARY:Harnessing amine-boranes as tunable alkyl radical precursors.
LOCATION:Chemistry A101
TZID:America/Denver
DTSTART:20260518T160000
UID:2026-05-15-04-55-44@natsci.colostate.edu
DTSTAMP:20260515T045544
Description:Seminar Abstract:\n\nAmines are among the most prevalent functi
 onal group encountered in biologically active molecules and synthetic chem
 istry. Traditionally treated as synthetic end points\, amines have recentl
 y emerged as valuable alkyl radical precursors. Central to these transform
 ations is activation of the nitrogen center to reduce the Csp3–N bond di
 ssociation energy. One activation strategy involves the in situ formation 
 of amine-borane adducts. These complexes undergo facile hydrogen atom abst
 raction at the boron center and subsequent β-scission across the C–N bo
 nd\, forming a nucleophilic alkyl radical. However\, the capacity of these
  amine-boranes to undergo conventionally difficult C–N β-scission remai
 ns largely unexplored. Employing cyclic amines under this regime would pro
 vide access to ring-opened alkyl radical species. Subsequent reduction and
  reaction with diiodomethane would afford a one-carbon ring-expansion of s
 aturated nitrogen heterocycles. This transformation would deliver homologa
 ted analogs of structurally complex cyclic amines in a single step. Additi
 onally\, a direct and general method for deaminative fluorination could be
  realized by employing N-fluorosulfonamides as a modular fluorine source w
 ith amine-boranes via copper-catalysis. 4:00 pm
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