Applications of Friedel–Crafts reactions in total synthesis of natural products

Heravi, Majid M.; Zadsirjan, Vahideh; Saedi, Pegah; Momeni, Tayebeh

doi:10.1039/c8ra07325b

Cited by 84 publications

(39 citation statements)

References 631 publications

(501 reference statements)

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“…32 Its usefulness became apparent from one of the organic chemistry's earliest and most ground-breaking discoveries, Friedel-Craft's acylation. 33–35 Over the years, aluminium lost its way as a catalyst due to the frequent appearance and success of transition metals in the catalysis of various organic reactions. As discussed earlier, due to the need for highly reactive reagents, very reactive NaBH 4 or BH 3 which can be directly added is traditionally used as a hydroboration reagent.…”

Section: Why Aluminium and How It Stole The Showmentioning

confidence: 99%

Aluminium complexes: next-generation catalysts for selective hydroboration

2022

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Section: Why Aluminium and How It Stole The Showmentioning

confidence: 99%

Aluminium complexes: next-generation catalysts for selective hydroboration

2022

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“…Traditional methods include reactions of acyl electrophiles with organometallic reagents (such as Grignard reagent) or electron-rich arenes (Friedel–Crafts reactions, under catalysis of Brønsted or Lewis acids) (Fig. 1a , top) 3 – 6 . Metal-catalyzed couplings of acyl electrophiles with nucleophiles 7 – 11 or electrophiles 12 have also been developed (Fig.…”

Section: Introductionmentioning

confidence: 99%

Carbene and photocatalyst-catalyzed decarboxylative radical coupling of carboxylic acids and acyl imidazoles to form ketones

et al. 2022

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The carbene and photocatalyst co-catalyzed radical coupling of acyl electrophile and a radical precursor is emerging as attractive method for ketone synthesis. However, previous reports mainly limited to prefunctionalized radical precursors and two-component coupling. Herein, an N-heterocyclic carbene and photocatalyst catalyzed decarboxylative radical coupling of carboxylic acids and acyl imidazoles is disclosed, in which the carboxylic acids are directly used as radical precursors. The acyl imidazoles could also be generated in situ by reaction of a carboxylic acid with CDI thus furnishing a formally decarboxylative coupling of two carboxylic acids. In addition, the reaction is successfully extended to three-component coupling by using alkene as a third coupling partner via a radical relay process. The mild conditions, operational simplicity, and use of carboxylic acids as the reacting partners make our method a powerful strategy for construction of complex ketones from readily available starting materials, and late-stage modification of natural products and medicines.

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“…The concept laid out in these pioneering studies proved to be a powerful one, whose generality was further honed over the following century. Today, these reactions remain a main‐stay of the synthetic organic chemist, thanks, in part, to the development of milder methodologies [2] . In particular, the development of many new metal‐ and organo‐catalysed processes has enabled the formation of both benzylic and adjacent stereo‐centres, which appear frequently in biologically active compounds [3] .…”

Section: Introductionmentioning

confidence: 99%

Biocatalytic Friedel‐Crafts Reactions

Leveson-Gower

Roelfes

2022

ChemCatChem

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Friedel-Crafts alkylation and acylation reactions are important methodologies in synthetic and industrial chemistry for the construction of aryl-alkyl and aryl-acyl linkages that are ubiquitous in bioactive molecules. Nature also exploits these reactions in many biosynthetic processes. Much work has been done to expand the synthetic application of these enzymes to unnatural substrates through directed evolution. The promise of such biocatalysts is their potential to supersede inefficient and toxic chemical approaches to these reactions, with mild operating conditions -the hallmark of enzymes. Complementary work has created many bio-hybrid Friedel-Crafts catalysts consisting of chemical catalysts anchored into biomolecular scaffolds, which display many of the same desirable characteristics. In this Review, we summarise these efforts, focussing on both mechanistic aspects and synthetic considerations, concluding with an overview of the frontiers of this field and routes towards more efficient and benign Friedel-Crafts reactions for the future of humankind.

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Applications of Friedel–Crafts reactions in total synthesis of natural products

Abstract: In this review, we try to underscore the applications of intermolecular and intramolecular FC reactions in the total syntheses of natural products and complex molecules, exhibiting diverse biological properties.

Cited by 84 publications

References 631 publications

Aluminium complexes: next-generation catalysts for selective hydroboration

Aluminium complexes: next-generation catalysts for selective hydroboration

Carbene and photocatalyst-catalyzed decarboxylative radical coupling of carboxylic acids and acyl imidazoles to form ketones

Biocatalytic Friedel‐Crafts Reactions

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