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SUMMARY:New Reagents to Facilitate Pentafluorosulfanylation of Arenes
LOCATION:Chemistry A101
TZID:America/Denver
DTSTART:20220606T160000
UID:2026-04-21-08-06-18@natsci.colostate.edu
DTSTAMP:20260421T080618
Description:About the Talk:\n\nThe beneficial effects of fluorine substitut
 ion on the ADME properties of drugs has been widely recognized and its pre
 sence in pharmaceuticals and agrochemicals has increased dramatically due 
 to the development of reagents for facile fluorination and trifluoromethyl
 ation. Conversely\, the pentafluorosulfanyl (–SF5) group remains underex
 plored due to the challenges of working with traditional gaseous and highl
 y toxic –SF5 precursors. The –SF5 group possesses both high electroneg
 ativity and high lipophilicity\, has high thermal and hydrolytic stability
 \, and has shown enhanced pharmacological properties of drugs when compare
 d to trifluoromethyl substituted analogs. Current access to aryl–SF5 com
 pounds is limited mainly to the simple thiophenols and derivatives amenabl
 e to the harsh oxidative-fluorination conditions necessary to generate the
  –SF5 group. Recent efforts have realized the ability of phenothiazine p
 hotocatalysts to reduce nontoxic SF6 to form a SF5 radical and fluoride an
 ion after mesolytic cleavage. Ultimately\, the photolytically generated SF
 5 radical was only shown to add anti-markovnikov to styrenes. The developm
 ent of an easy-to-handle SF5 precursor that undergoes reversible photo-pro
 moted homolysis may help spur the development of pentafluorosulfanylation 
 methodologies. To that end\, development of a competent radical trap in c
 onjunction with a N-arylphenothiazine photocatalyst may allow for the red
 uction of SF6 and subsequent trapping of the generated SF5 radical to crea
 te a stable\, photocleavable SF5 proradical reagent. 4:00 pm
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