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Friedel-Crafts Alkylation of Indoles with Trichloroacetimidates.

ABSTRACT: Substituted indole scaffolds are often utilized in medicinal chemistry as they regularly possess significant pharmacological activity. Therefore the development of simple, inexpensive and efficient methods for alkylating the indole heterocycle continues to be an active research area. Reported are reactions of trichloroacetimidate electrophiles and indoles to address the challenges of accessing alkyl decorated indole structures. These alkylations perform best when either the indole or the imidate is functionalized with electron withdrawing groups to avoid polyalkylation.

SUBMITTER: Suzuki T

PROVIDER: S-EPMC6720118 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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Friedel-Crafts Alkylation of Indoles with Trichloroacetimidates.

Suzuki Tamie T Chisholm John D JD

Tetrahedron letters 20190403 19

Substituted indole scaffolds are often utilized in medicinal chemistry as they regularly possess significant pharmacological activity. Therefore the development of simple, inexpensive and efficient methods for alkylating the indole heterocycle continues to be an active research area. Reported are reactions of trichloroacetimidate electrophiles and indoles to address the challenges of accessing alkyl decorated indole structures. These alkylations perform best when either the indole or the imidate ...[more]

PMID: 31481819

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Project description:Heterogeneous Zr-Mont catalyst prepared by a simple protocol was employed for the production of diesel fuel precursors via Friedel-Crafts (FC) alkylation of petroleum-derived arenes (e.g., mesitylene, xylene, and toluene) with biomass-derived 5-(hydroxymethyl)furfural (HMF), HMF derivatives, and carbohydrates. Initially, several acidic catalysts were screened for the FC alkylation of mesitylene with HMF in nitroethane solvent. Among all, Zr-Mont catalyst gave an exceptionally high yield (80%) of mesitylmethylfurfural (MMF). The catalytic activity of Zr-Mont was also evaluated for the alkylation of different petroleum-derived arenes with ester/halogen derivatives of HMF. Suitable acid strength and high surface area of Zr-Mont were its major attributes to make it the most efficient solid acid catalyst for this FC reaction. Even after several reuses, the catalytic activity of Zr-Mont was found to be consistent, which was also evidenced by the acidity measurements of fresh and reused Zr-Mont catalysts by temperature-programmed desorption of ammonia and pyridine Fourier transform infrared spectroscopy techniques. Direct conversion of glucose to diesel fuel precursors was also attempted over Zr-Mont catalyst in mesitylene and polar nonacidic solvents at 150 °C. However, the activity of Zr-Mont catalyst was limited for glucose dehydration to HMF and MMF did not form. When the same experiment was performed in formic acid medium, MMF was produced in 34% yield. After the addition of formic acid, the reaction becomes biphasic which contains mesitylene as an organic phase and formic acid as an aqueous phase. Formic acid worked as a solvent, reactant, and cocatalyst, whereas mesitylene worked as a reactant and product extraction phase to enable easy product isolation. With this strategy, other diesel fuel precursors were also produced in 26-30% yields from glucose and different arenes. Similar strategy was successfully extended for the conversion of sucrose to diesel fuel precursors.

Dataset Information

Friedel-Crafts Alkylation of Indoles with Trichloroacetimidates.

Publications

Friedel-Crafts Alkylation of Indoles with Trichloroacetimidates.

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