Iron-Catalyzed Carbamoylation of Enamides with Formamides as a Direct Approach to N-Acyl Enamine Amides

Zhen Yao Shen; Jun Kee Cheng; Cong Wang; Chao Yuan; Teck Peng Loh; Xu Hong Hu

doi:10.1021/acscatal.9b02635

Iron-Catalyzed Carbamoylation of Enamides with Formamides as a Direct Approach to N-Acyl Enamine Amides

Zhen Yao Shen, Jun Kee Cheng, Cong Wang, Chao Yuan, Teck Peng Loh, Xu Hong Hu^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

48 Citations (Scopus)

Abstract

The robustness of iron catalysis enabling the oxidative coupling reactions of enamides with formamides is described. Routing from readily accessible feedstocks, the efficient approach is implemented to furnish a broad array of value-added N-acyl enamine amide derivatives, which serve as versatile precursors of biologically relevant N-heterocycles including pyrimidin-4-ones and 4-hydroxypyridin-2-ones. Preliminary mechanistic studies supported the notion that this direct carbamoylation reaction proceeded through an aminoacyl radical species.

Original language	English
Pages (from-to)	8128-8135
Number of pages	8
Journal	ACS Catalysis
Volume	9
Issue number	9
DOIs	https://doi.org/10.1021/acscatal.9b02635
Publication status	Published - Sept 6 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019 American Chemical Society.

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

enamide
formamide
iron
oxidative coupling
radicals

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10.1021/acscatal.9b02635

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title = "Iron-Catalyzed Carbamoylation of Enamides with Formamides as a Direct Approach to N-Acyl Enamine Amides",

abstract = "The robustness of iron catalysis enabling the oxidative coupling reactions of enamides with formamides is described. Routing from readily accessible feedstocks, the efficient approach is implemented to furnish a broad array of value-added N-acyl enamine amide derivatives, which serve as versatile precursors of biologically relevant N-heterocycles including pyrimidin-4-ones and 4-hydroxypyridin-2-ones. Preliminary mechanistic studies supported the notion that this direct carbamoylation reaction proceeded through an aminoacyl radical species.",

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AU - Shen, Zhen Yao

AU - Cheng, Jun Kee

AU - Wang, Cong

AU - Yuan, Chao

AU - Loh, Teck Peng

AU - Hu, Xu Hong

PY - 2019/9/6

Y1 - 2019/9/6

N2 - The robustness of iron catalysis enabling the oxidative coupling reactions of enamides with formamides is described. Routing from readily accessible feedstocks, the efficient approach is implemented to furnish a broad array of value-added N-acyl enamine amide derivatives, which serve as versatile precursors of biologically relevant N-heterocycles including pyrimidin-4-ones and 4-hydroxypyridin-2-ones. Preliminary mechanistic studies supported the notion that this direct carbamoylation reaction proceeded through an aminoacyl radical species.

AB - The robustness of iron catalysis enabling the oxidative coupling reactions of enamides with formamides is described. Routing from readily accessible feedstocks, the efficient approach is implemented to furnish a broad array of value-added N-acyl enamine amide derivatives, which serve as versatile precursors of biologically relevant N-heterocycles including pyrimidin-4-ones and 4-hydroxypyridin-2-ones. Preliminary mechanistic studies supported the notion that this direct carbamoylation reaction proceeded through an aminoacyl radical species.

KW - enamide

KW - formamide

KW - iron

KW - oxidative coupling

KW - radicals

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Iron-Catalyzed Carbamoylation of Enamides with Formamides as a Direct Approach to N-Acyl Enamine Amides

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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