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X-WR-CALNAME:Organic Chemistry Special Seminar
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SUMMARY:Alcohol and Amine Derivatives Guide Position-Selective C-H Functio
 nalization Reactions
DTSTART;TZID=America/Los_Angeles:20190507T160000
DTEND;TZID=America/Los_Angeles:20190507T170000
DTSTAMP:20241112T120621Z
UID:Organic Chemistry Special Seminar@Tue May  7 16:00:00 2019@main.oscweb
 .caltech.edu
CATEGORIES:
DESCRIPTION:Jenny Roizen\, Assistant Professor\, Department of Chemistry\,
  Duke University\nNitrogen-centered radical applications remain underexplo
 red due to the lack of convenient methods for their generation. We have im
 proved access to nitrogen-centered radicals based on oxidation of sulfamat
 e esters and sulfamides to provide access to nitrogen-centered radicals th
 at can guide C-H functionalization reactions.\nOur directed technology has
  been inspired by one of the most reliable and powerful known reactions to
  guide C–H functionalization reactions: the Hofmann-Loffler-Freytag (HLF
 ) reaction\, which uses amines or amides as directing groups. Like many of
  the most robust radical-mediated technologies to direct the activation of
  tertiary and secondary centers\, the HLF reaction is guided through 1\,5-
 hydrogen-atom transfer (HAT) processes\, which proceeds through a kinetica
 lly-favorable six-membered ring transition state. By contrast\, few report
 s describe 1\,6-HAT with a cleavable linker\, such as a sulfamate ester\, 
 and there are no general strategies to enable masked alcohols to direct fu
 nctionalization of aliphatic gamma-C-H centers. This talk will outline thi
 s novel strategy to harness alcohols to replace C-H bonds at gamma-C-H cen
 ters\, which are not generally accessible to directed functionalization. T
 his talk will highlight the first generalizable synthetic strategy to func
 tionalize gamma-C-H bonds based on masked alcohols.
LOCATION:Noyes 153 (J. Holmes Sturdivant Lecture Hall)
URL:https://www.caltech.edu/campus-life-events/calendar/organic-chemistry-
 special-seminar-2
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