Abstract
The synthesis of substituted pyrroles from substituted β-alkynyl ketones using catalytic silver triflate or a mixture of gold(I) chloride, triphenylphosphine and silver triflate in moderate to good yields is reported. Reasonable tolerance towards functional groups is observed. Interestingly, while the reaction proceeds well in toluene, CH2Cl2 and i-PrOH, it fails in THF. Other silver sources (e.g., AgBF4, AgOCOCF3) gave comparable yields. For reactive amines, the two catalyst systems show comparable results, even though the AuCl/AgOTf/PPh3 mixture seems to be thermally more stable. PtCl2 and FeCl3 give only traces of the pyrrole products. No pyrrole product was formed when tert-butylamine was used. Using the same reaction conditions, the cyclization of imines to bicylic pyrroles was achieved in moderate yields.
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