Abstract
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.
Highlights
Pyrroles are known to be important structural moieties appearing in natural products, synthetic drugs, agrochemicals, and functional materials (Figure 1) [1,2,3,4]
We have recently reported that N-perfluoroalkyl-1,2,3-triazoles [18] undergo rhodium-catalyzed transannulation reactions leading to various nitrogen heterocycles, such as imidazoles, Beilstein J
Taking inspiration from the work of Gevorgyan (Scheme 1h) [11], we report our recent results on the rhodium-catalyzed transannulation of N-perfluoroalkyl-1,2,3triazoles with terminal alkynes leading to unusually substituted N-perfluoroalkylpyrroles
Summary
Pyrroles are known to be important structural moieties appearing in natural products, synthetic drugs, agrochemicals, and functional materials (polymers, dyes, films, etc.) (Figure 1) [1,2,3,4]. N-sulfonyl-1,2,3-triazoles, conveniently prepared by [3 + 2] cycloadditions of terminal alkynes with sulfonyl azides, have been used as the precursors to N-sulfonylindoles by transition-metal-catalyzed transannulation reactions. In the presence of Rh(II) or Ni(0) catalysts the triazole ring-opening takes place and intermediate highly electrophilic metal-bound iminocarbenes form. A variety of pyrroles have been prepared starting from N-sulfonyl-1,2,3-triazoles (Scheme 1) [11,12,13,14,15,16,17].
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