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

16 April 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

Pyrrole Synthesis
copper catalysis
heterocycles

Supplementary materials

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SI Pyrrole Synthesis 1 Experiment
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SI Pyrrole Synthesis 2 Calculation
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