Direct dehydrative N-pyridinylation of amides.
Electrophilic activation of secondary amides with trifluoromethanesulfonic anhydride in the presence of 2-fluoropyridine followed by introduction of a pyridine N-oxide derivative and warming affords the corresponding N-pyridinyl tertiary amide derivatives. A mechanism supported by in situ monitoring and deuterium labeling experiments is discussed.
Medley
Jonathan William
JW
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Movassaghi
Mohammad
M
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D000812:Anhydrides / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry
C521930:2-fluoropyridine; D000577:Amides; D000812:Anhydrides; D008698:Mesylates; D011725:Pyridines; C013229:pyridine N-oxide; C012077:trifluoromethanesulfonic acid