Innate C-H trifluoromethylation of heterocycles

Direct methods for the trifluoromethylation of heteroaromatic systems are in extremely high demand in nearly every sector of chemical industry. Here we report the discovery of a general procedure using a benchtop stable trifluoromethyl radical source that functions broadly on a variety of electron deficient and rich heteroaromatic systems and demonstrates high functional group tolerance. This C-H trifluoromethylation protocol is operationally simple (avoids gaseous CF(3)I), scalable, proceeds at ambient temperature, can be used directly on unprotected molecules, and is demonstrated to proceed at the innately reactive positions of the substrate. The unique and orthogonal reactivity of the trifluoromethyl…

• NS
  National Science Foundation
• A
  Amgen
• BS
  Bristol-Myers Squibb
• P
  Pfizer
• DA
  Deutscher Akademischer Austauschdienst
• NI
  National Institutes of Health

  Award: GM-073949
• JS
  Japan Society for the Promotion of Science
• NI
  National Institute of General Medical Sciences

  Award: GM-073949