Synthesis of Pyrroles Through the CuH-Catalyzed Coupling of Enynes and Nitriles



Herein, we describe an efficient method to prepare polysubstituted pyrroles via a copper-hydride (CuH)-catalyzed enyne-nitrile coupling reaction. This protocol accommodates both aromatic and aliphatic substituents and a broad range of functional groups, providing a variety of N-H pyrroles in good yields and with high regioselectivity. We propose that the Cu-based catalyst promotes both the initial reductive coupling and subsequent cyclization steps. Density functional theory (DFT) calculations were performed to elucidate the reaction mechanism.


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Supplementary material

Thumbnail image of SI_Pyrrole Synthesis_1_Experiment.pdf
SI Pyrrole Synthesis 1 Experiment
Thumbnail image of SI_Pyrrole Synthesis_2_Calculation.pdf
SI Pyrrole Synthesis 2 Calculation