Carbene-catalyzed asymmetric Friedel–Crafts alkylation-annulation sequence and rapid synthesis of indole-fused polycyclic alkaloids

Anwar, Muhammad U.; Yang, Shuang; Xu, Weici; Liu, Jinggong; Perveen, Saima; Kong, Xiangbin; Zehra, Syeda Tazeen; Fang, Xinqiang

doi:10.1038/s42004-019-0188-2

Cited by 15 publications

(15 citation statements)

References 63 publications

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“…The catalytic activity of commercial clay is based on the Friedel–Crafts alkylation reaction, which is shown in Fig. 5 60,61 . This reaction has low conversion at low temperatures 41,62 and Lewis acid sites play a pivotal role in this reaction 7,38 .…”

Section: Resultsmentioning

confidence: 99%

Optimizing temperature and introducing new process arrangements for elevating clay's longevity based on the known poisons in the separation process of trace olefins from aromatics

Rouhani

Farhadi

Kenari

et al. 2021

J of Chemical Tech & Biotech

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BACKGROUND The clay treatment widely utilized to reduce unsaturated components in aromatic stream has a detrimental effect on catalyst lifetime. Due to the short lifetime of commercial clay, a huge number of studies have been carried out to address this problem over the last decade. This study aims to optimize the temperature for longer serviceability of clay by removal of unsaturated aliphatic components from aromatic streams through the adsorption and catalytic properties of clay. A novel process arrangement is introduced by scheduling the reuse of deactivated clay that is discarded after deactivation. RESULTS Results showed that the suitable range of temperature for olefin removal is 155–205 °C, and the optimum temperature with the lowest operational cost was 185 °C, which is then gradually elevated to 205 °C. CONCLUSION The new process arrangements utilize these results and elevate clay's lifetime by almost 3.5 times, leading to an economical solution on an industrial scale. © 2021 Society of Chemical Industry (SCI).

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Section: Resultsmentioning

confidence: 99%

Optimizing temperature and introducing new process arrangements for elevating clay's longevity based on the known poisons in the separation process of trace olefins from aromatics

Rouhani

Farhadi

Kenari

et al. 2021

J of Chemical Tech & Biotech

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“…At the end of this chapter, it is worth mentioning a few more non-obvious approaches to the asymmetric Friedel-Crafts reaction. They are for sure the use of N-heterocyclic carbenes as catalysts in the synthesis of indole-fused polycyclic alcohols [56], guanosinebased self-assembly as catalytic system [57], and various DNA-employing catalytic systems [58][59][60].…”

Section: Asymmetric Friedel-crafts Reactionsmentioning

confidence: 99%

Recent Advances in Selected Asymmetric Reactions Promoted by Chiral Catalysts: Cyclopropanations, Friedel–Crafts, Mannich, Michael and Other Zinc-Mediated Processes—An Update

2021

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The main purpose of this review article is to present selected asymmetric synthesis reactions in which chemical and stereochemical outcomes are dependent on the use of an appropriate chiral catalyst. Optically pure or enantiomerically enriched products of such transformations may find further applications in various fields. Among an extremely wide variety of asymmetric reactions catalyzed by chiral systems, we are interested in: asymmetric cyclopropanation, Friedel–Crafts reaction, Mannich and Michael reaction, and other stereoselective processes conducted in the presence of zinc ions. This paper describes the achievements of the above-mentioned asymmetric transformations in the last three years. The choice of reactions is related to the research that has been carried out in our laboratory for many years.

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“…In recent years, there has been growing interest in the field of N-heterocyclic carbene (NHC) catalysis. The functionalization of the indole core via various NHC-intermediates has been reported by several research groups [36][37][38][39][40]. There are only two articles dedicated to the N-functionalization of indoles [41,42].…”

Section: N-heterocyclic Carbene-mediated Cyclizationsmentioning

confidence: 99%

Enantioselective Catalytic Synthesis of N-alkylated Indoles

Trubitsõn

Kanger

2020

Symmetry

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During the past two decades, the interest in new methodologies for the synthesis of chiral N-functionalized indoles has grown rapidly. The review illustrates efficient applications of organocatalytic and organometallic strategies for the construction of chiral α-N-branched indoles. Both the direct functionalization of the indole core and indirect methods based on asymmetric N-alkylation of indolines, isatins and 4,7-dihydroindoles are discussed.

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Carbene-catalyzed asymmetric Friedel–Crafts alkylation-annulation sequence and rapid synthesis of indole-fused polycyclic alkaloids

Cited by 15 publications

References 63 publications

Optimizing temperature and introducing new process arrangements for elevating clay's longevity based on the known poisons in the separation process of trace olefins from aromatics

Optimizing temperature and introducing new process arrangements for elevating clay's longevity based on the known poisons in the separation process of trace olefins from aromatics

Recent Advances in Selected Asymmetric Reactions Promoted by Chiral Catalysts: Cyclopropanations, Friedel–Crafts, Mannich, Michael and Other Zinc-Mediated Processes—An Update

Enantioselective Catalytic Synthesis of N-alkylated Indoles

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