Synthesis of Pyrroles through the CuH-Catalyzed Coupling of Enynes and Nitriles
Author(s)
Zhou, Yujing; Zhou, Lin; Jesikiewicz, Luke T; Liu, Peng; Buchwald, Stephen Leffler
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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. Copyright © 2020 American Chemical Society.
Date issued
2020-05Department
Massachusetts Institute of Technology. Department of ChemistryJournal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Zhou, Yujing et al., "Synthesis of Pyrroles through the CuH-Catalyzed Coupling of Enynes and Nitriles." Journal of the American Chemical Society 142, 22 (June 2020): 9908–14 ©2020 Authors
Version: Original manuscript
ISSN
1520-5126