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Direct heterobenzylic fluorination, difluorination and trifluoromethylthiolation with dibenzenesulfonamide derivatives.
Meanwell, Michael; Adluri, Bharani Shashank; Yuan, Zheliang; Newton, Josiah; Prevost, Philippe; Nodwell, Matthew B; Friesen, Chadron M; Schaffer, Paul; Martin, Rainer E; Britton, Robert.
Afiliación
  • Meanwell M; Department of Chemistry , Simon Fraser University , Burnaby , British Columbia V5A 1S6 , Canada . Email: rbritton@sfu.ca.
  • Adluri BS; Department of Chemistry , Simon Fraser University , Burnaby , British Columbia V5A 1S6 , Canada . Email: rbritton@sfu.ca.
  • Yuan Z; Department of Chemistry , Simon Fraser University , Burnaby , British Columbia V5A 1S6 , Canada . Email: rbritton@sfu.ca.
  • Newton J; Life Science Division , TRIUMF , Vancouver , BC V6T 2A3 , Canada.
  • Prevost P; Department of Chemistry , Simon Fraser University , Burnaby , British Columbia V5A 1S6 , Canada . Email: rbritton@sfu.ca.
  • Nodwell MB; Department of Chemistry , Trinity Western University , Langley , British Columbia V2Y 1Y1 , Canada.
  • Friesen CM; Department of Chemistry , Simon Fraser University , Burnaby , British Columbia V5A 1S6 , Canada . Email: rbritton@sfu.ca.
  • Schaffer P; Department of Chemistry , Simon Fraser University , Burnaby , British Columbia V5A 1S6 , Canada . Email: rbritton@sfu.ca.
  • Martin RE; Department of Chemistry , Trinity Western University , Langley , British Columbia V2Y 1Y1 , Canada.
  • Britton R; Life Science Division , TRIUMF , Vancouver , BC V6T 2A3 , Canada.
Chem Sci ; 9(25): 5608-5613, 2018 Jul 07.
Article en En | MEDLINE | ID: mdl-30061993
Functionalization of heterocyclic scaffolds with mono- or difluoroalkyl groups provides unique opportunities to modulate drug pKa, influence potency and membrane permeability, and attenuate metabolism. While advances in the addition of fluoroalkyl radicals to heterocycles have been made, direct C(sp3)-H heterobenzylic fluorination is comparatively unexplored. Here we demonstrate both mono- and difluorination of a range of alkyl heterocycles using a convenient process that relies on transient sulfonylation by the electrophilic fluorinating agent N-fluorobenzenesulfonimide. We also report heterobenzylic trifluoromethylthiolation and 18F-fluorination, providing a suite of reactions for late-stage C(sp3)-H functionalization of drug leads and radiotracer discovery.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Sci Año: 2018 Tipo del documento: Article Pais de publicación: Reino Unido
Texto completo
Añadir a Mi BVS
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XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Sci Año: 2018 Tipo del documento: Article Pais de publicación: Reino Unido