Synthesis of N-perfluoroalkyl-3,4-disubstituted pyrroles by rhodium-catalyzed transannulation of N-fluoroalkyl-1,2,3-triazoles with terminal alkynes

The rhodium-catalyzed transannulation of N-perfluoroalkyl-1,2,3-triazoles with aromatic and aliphatic terminal alkynes under microwave heating conditions afforded N-perfluoroalkyl-3,4-disubstituted pyrroles (major products) and N-fluoroalkyl-2,4-disubstituted pyrroles (minor products). The observed selectivities in the case of the reactions with aliphatic alkynes were high.

Automated summary

The rhodium-catalyzed transannulation reaction between N-perfluoroalkyl-1,2,3-triazoles and aromatic or aliphatic terminal alkynes under microwave heating conditions selectively produced N-perfluoroalkyl-3,4-disubstituted pyrroles as major products and N-fluoroalkyl-2,4-disubstituted pyrroles as minor products. High selectivity was observed particularly in reactions involving aliphatic alkynes.