Pyrrole synthesis catalyzed by AgOTf or cationic Au(I) complexes.
Either silver trifluoromethanesulfonate or a mixture of gold(I) chloride, silver trifluoromethanesulfonate, and triphenylphosphine catalyze the formation of pyrroles from substituted beta-alkynyl ketones and amines. The reactions proceed by using 5 mol % of catalyst with yields of isolated pyrroles ranging from 13% to 92%. Sixteen examples are used to compare the effectiveness of each catalyst.
Harrison
Tyler J
TJ
Department of Chemistry, 2036 Main Mall, University of British Columbia, Vancouver, BC, Canada, V6T 1Z1.
Kozak
Jennifer A
JA
Corbella-Pané
Montserrat
M
Dake
Gregory R
GR
D000588:Amines / Q000737:chemistry; D002384:Catalysis; D017612:Gold Compounds / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis*
D000588:Amines; D017612:Gold Compounds; D007659:Ketones; D008698:Mesylates; D011758:Pyrroles; C012077:trifluoromethanesulfonic acid