Scandium catalysed stereoselective thio-allylation of allenyl-imidates

Parodi, Adriano; Battaglioli, Simone; Liu, Yang; Monari, Magda; Marín‐Luna, Marta; López, Carlos Silva; Bandini, Marco

doi:10.1039/c9cc04302k

Cited by 4 publications

(1 citation statement)

References 29 publications

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“…8 In continuation with our ongoing interests in graphene oxide (GO) mediated organic transformations, 9 we herein focus on the realization of a ligand-free reduced graphene oxide-(rGO) supported Ni(0) nanocomposite 10 for the realization of a still underdeveloped methodology in the metal-catalyzed crosscoupling area: the Csp 2 -S bond-forming protocols. 11,12 In particular, we envisioned that the nucleation activity of the oxygenated functional groups present in the rGO towards metal Template for SYNTHESIS Thieme nanoparticles, combined with a dedicated modulation of NP growth/dispersion, could provide a suitable platform for the realization of a catalytically active Ni(0)-based heterogeneous promoter for challenging cross-coupling reactions (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

NiNP@rGO Nanocomposites as Heterogeneous Catalysts for Thiocarboxylation Cross-Coupling Reactions

et al. 2021

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A new type of ligand-free Ni-nanoparticles supported on rGO (size distribution average d = 9 ± 3 nm) is prepared and fully characterized via morphological (Fe-SEM), structural (P-XRD, HR-TEM) and spectroscopic (ICP-EOS, XPS) analysis tools. The metal composite was effectively employed in the unprecedented heterogeneously Ni-assisted cross-coupling reaction of aryl/vinyl iodides and thiocarboxylates. A range of sulphur-containing aryl as well as vinyl derivatives (15 examples) was achieved in high yields (up to 82%), mild reaction conditions and wide functional group tolerance.

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Section: Introductionmentioning

confidence: 99%

NiNP@rGO Nanocomposites as Heterogeneous Catalysts for Thiocarboxylation Cross-Coupling Reactions

et al. 2021

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Electrochemical Synthesis of Itaconic Acid Derivatives via Chemodivergent Single and Double Carboxylation of Allenes with CO₂

Brunetti,

Garbini,

Autuori

et al. 2024

Chemistry A European J

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Leveraging electrochemistry, a new synthesis of non‐natural derivatives of itaconic acid is proposed by utilizing carbon dioxide (CO2) as a valuable C1 synthon. An electrochemical cross‐electrophile coupling between allenoates and CO2 was targeted, allowing for the synthesis of both mono‐ and di‐carboxylation products in a catalyst‐ and additive‐free environment (yields up to 87%, 30 examples). Elaboration of the model mono‐carboxylation product, and detailed cyclovoltammetric, as well as mechanistic analyses complete the present investigation.

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A leap forward in sulfonium salt and sulfur ylide chemistry

Fan

Tan

Liu

et al. 2021

Chinese Chemical Letters

110

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Scandium catalysed stereoselective thio-allylation of allenyl-imidates

Abstract: The site-selective thio-allylation of electron-deficient 1,2-dienes is documented under scandium catalysis.

Cited by 4 publications

References 29 publications

NiNP@rGO Nanocomposites as Heterogeneous Catalysts for Thiocarboxylation Cross-Coupling Reactions

NiNP@rGO Nanocomposites as Heterogeneous Catalysts for Thiocarboxylation Cross-Coupling Reactions

Electrochemical Synthesis of Itaconic Acid Derivatives via Chemodivergent Single and Double Carboxylation of Allenes with CO₂

A leap forward in sulfonium salt and sulfur ylide chemistry

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Scandium catalysed stereoselective thio-allylation of allenyl-imidates

Abstract: The site-selective thio-allylation of electron-deficient 1,2-dienes is documented under scandium catalysis.

Cited by 4 publications

References 29 publications

NiNP@rGO Nanocomposites as Heterogeneous Catalysts for Thiocarboxylation Cross-Coupling Reactions

NiNP@rGO Nanocomposites as Heterogeneous Catalysts for Thiocarboxylation Cross-Coupling Reactions

Electrochemical Synthesis of Itaconic Acid Derivatives via Chemodivergent Single and Double Carboxylation of Allenes with CO2

A leap forward in sulfonium salt and sulfur ylide chemistry

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Product

Resources

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Electrochemical Synthesis of Itaconic Acid Derivatives via Chemodivergent Single and Double Carboxylation of Allenes with CO₂