Synthesis and reactivity of α-sulfenyl-β-chloroenones, including oxidation and Stille cross-coupling to form chalcone derivatives

Kearney, Aoife M.; Murphy, Linda; Murphy, Colin C.; Eccles, Kevin S.; Lawrence, Simon E.; Collins, Stuart G.; Maguire, Anita R.

doi:10.1016/j.tet.2021.132091

Cited by 5 publications

(4 citation statements)

References 27 publications

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“…80 Moreover, the selective formation of Z sulfenyl chalcones 64 was reported by using Stille cross-coupling with the Z α-sulfenyl-β-chloroenones 62, while the E α-sulfenylβ-chloroenones did not react under the same conditions (Scheme 17). 81,82 3.11. Decarboxylative cross-coupling Jiang et al described the synthesis of different chalcones 67 by the decarboxylation cross-coupling reaction of α-oxo carboxylic acid 65 and cinnamic acid derivatives 66 in an aqueous solution using an iron-facilitated oxidative radical, 83 as shown in Scheme 18.…”

Section: Stille Coupling Reactionsmentioning

confidence: 99%

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Synthesis, reactions and application of chalcones: a systematic review

2023

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Section: Stille Coupling Reactionsmentioning

confidence: 99%

“…Moreover, the selective formation of Z sulfenyl chalcones 64 was reported by using Stille cross-coupling with the Z α-sulfenyl-β-chloroenones 62 , while the E α-sulfenyl-β-chloroenones did not react under the same conditions (Scheme 17). 81,82…”

Section: Synthesis Of Chalconesmentioning

confidence: 99%

Synthesis, reactions and application of chalcones: a systematic review

2023

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“…Chalcones are produced when aromatic aldehydes and acetophenones are combined in the presence of a catalyst. There are currently several different ways to synthesize numerous chalcone analogs like Claisen–Schmidt's condensation, [1] Allan‐Robinson Condensation, [2] Friedel‐Crafts Acylation, [3] Julia‐Kocienski Olefination, [4] Meyer‐Schuster Rearrangement, [5] coupling reaction such as Suzuki‐Miyaura, [6] Sonogashira, [7] Heck, [8] Stille, [9] Hiyama coupling, [10] etc. These unsaturated carbonyl compounds have two electrophilic reactive centers because of the delocalization of electron density in the C=C−C=O system.…”

Section: Introductionmentioning

confidence: 99%

Naphthyl‐Based Chalcone Derivatives: A Multifaceted Player in Medicinal Chemistry

Mahesha,

Shetty

2024

ChemistrySelect

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Research has placed a great deal of emphasis on molecule development and discovery with substantial biological profiling in recent years. Despite the significant side effects, medicinal chemists have long strived to synthesize drug molecules with the highest level of therapeutic activity and the lowest possible level of toxicity. The naphthyl‐based chalcone derivatives have drawn attention due to their simple structures and wide range of pharmacological effects. The main focus of this review is to outline the biologically active molecules based on naphthyl moiety‐substituted chalcone derivatives developed over the years. A synopsis of pharmacological screening, including relevant structure‐activity relationships, action mechanisms, and possible therapeutic applications, is provided in this article. It is true that prospective hybrids combining the naphthyl moiety with different chalcone pharmacophores are needed to address drug resistance and improve specificity. Therefore, this review may be useful in the development and design of new, highly successful therapeutic drugs based on previously reported methodologies.

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“…These nucleophiles include enolate equivalents, enol silanes, ene-donors, silanes, electron-rich arenes, and turbo Grignards . Traditional syntheses of these β-keto sulfides include the reaction of mercaptans with α-haloketones or sulfenyl halides with enolates . An alternate route could employ umpolung reactivity, i.e., polarity inversion, to access an acyl anion equivalent as a carbon-based nucleophile for addition into the sulfenium (Figure B).…”

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confidence: 99%

Acyl Azolium–Photoredox-Enabled Synthesis of β-Keto Sulfides

et al. 2023

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α-Heteroatom functionalization is a key strategy for C–C bond formation in organic synthesis, as exemplified by the addition of a nucleophile to electrophilic functional groups, such as iminium ions; oxocarbenium ions; and their sulfur analogues, sulfenium ions. We envisioned a photoredox-enabled radical Pummerer-type reaction realized through the single-electron oxidation of a sulfide. Following this oxidative event, α-deprotonation would afford α-thio radicals that participate in radical–radical coupling reactions with azolium-bound ketyl radicals, thereby accessing a commonly proposed mechanistic intermediate of the radical–radical coupling en route to functionalized additive Pummerer products. This system provides a complementary synthetic approach to highly functionalized sulfurous products, including modification of methionine residues in peptides, and beckons further exploration in C–C bond formations previously limited in the standard two-electron process.

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Synthesis and reactivity of α-sulfenyl-β-chloroenones, including oxidation and Stille cross-coupling to form chalcone derivatives

Cited by 5 publications

References 27 publications

Synthesis, reactions and application of chalcones: a systematic review

Synthesis, reactions and application of chalcones: a systematic review

Naphthyl‐Based Chalcone Derivatives: A Multifaceted Player in Medicinal Chemistry

Acyl Azolium–Photoredox-Enabled Synthesis of β-Keto Sulfides

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