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Synthesis of Pyrroles through the CuH-Catalyzed Coupling of Enynes and Nitriles.

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.

SUBMITTER: Zhou Y

PROVIDER: S-EPMC8009196 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature

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Synthesis of Pyrroles through the CuH-Catalyzed Coupling of Enynes and Nitriles.

Zhou Yujing Y Zhou Lin L Jesikiewicz Luke T LT Liu Peng P Buchwald Stephen L SL

Journal of the American Chemical Society 20200519 22

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 w ...[more]

PMID: 32395998

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