Silver-Catalyzed Domino Reaction of CF3-Substituted N-Allenamides with Primary Amines for the Construction of 2-Amido-5-fluoropyrroles

被引：9

作者：

Hourtoule, Maxime ^{[1
]}

Miesch, Laurence ^{[1
]}

机构：

[1] CNRS UdS, UMR 7177, Inst Chim, Equipe Synth Organ & Phytochim, F-67081 Strasbourg, France

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 10期

关键词：

PYRROLE DERIVATIVES; HYDROAMINATION; FLUORINATION; CYCLIZATION; YNAMIDES; ANILINES; POTENT;

D O I：

10.1021/acs.orglett.3c00401

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report herein a domino reaction to construct 2-amido-5-fluoropyrroles from CF3-substituted N-allenamides. The in situ generated gem-difluorinated ene-ynamides derived from CF3-substituted N-allenamides, when subjected to silver catalysis with a primary amine, undergo simultaneous hydroamination of the ynamide moiety followed by a 5-endo-trig addition/beta-fluoride elimination sequence, enabling the construction of 2-amido-5-fluoropyrroles. This transformation features excellent functional group compatibility. By employing 2-aminophenols, functionalized benzo-oxazoles were produced.

引用

页码：1727 / 1731

页数：5

共 7 条

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[3] Silver-catalyzed [3+2] domino reaction: an efficient strategy to synthesize imidazole-5-carbaldehydes
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[4] THE MECHANISM OF THE SILVER-CATALYZED REACTION BETWEEN N,N-DIMETHYL-PARA-PHENYLENEDIAMINE AND [COIII(NH3)5CL]2+
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[5] Efficient synthesis of substituted pyrroles through Pd(OCOCF3)2-catalyzed reaction of 5-hexen-2-one with primary amines
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[6] Acetic Acid-Catalyzed Selective Synthesis of N-Substituted 2-Amino-3-Cyanopyrroles via a Three-Component Reaction Between Carbohydrates, Primary Amines and Malononitrile
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ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (09)
[7] REACTION OF 4-ETHOXY-2-PHENYL-2-OXAZOLIN-5-ONE WITH PRIMARY AMINES IN THE PRESENCE OF THIOLS - ONE-FLASK SYNTHESIS OF N-SUBSTITUTED 2-BENZOYLAMINO-3-ALKYLTHIO-2-PROPENAMIDES
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CHEMISTRY & INDUSTRY, 1986, (23) : 825 - 825

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