Synthesis of Pyrroles through the CuH-Catalyzed Coupling of Enynes and Nitriles
Name
Manuscript_Pyrrole Synthesis.pdf
Description
Submitted version
Size
1.31 MB
Format
Adobe PDF
Checksum (MD5)
22f4530ee0f6726d3ec8c13bfdcab5e0
Author(s)
Zhou, Yujing
Zhou, Lin
Jesikiewicz, Luke T
Liu, Peng
Buchwald, Stephen Leffler
Date Issued
May 2020
Journal
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
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. Copyright © 2020 American Chemical Society.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Creative Commons Attribution-Noncommercial-Share Alike
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DOI of Published Version
https://doi.org/10.1021/JACS.0C03859
