Brønsted acid-catalysed desilylative heterocyclisation to form substituted furans

Babcock, Emily G; Rahman, Md. Shafiqur; Taylor, James E.

doi:10.1039/d2ob01828d

Org. Biomol. Chem.

2023

DOI: 10.1039/d2ob01828d

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Brønsted acid-catalysed desilylative heterocyclisation to form substituted furans

Emily G Babcock

Md. Shafiqur Rahman

James E. Taylor

Abstract: Heterocyclisation of tert-butyldimethylsilyl (TBS) protected γ-hydroxy-α,β-unsaturated ketones catalysed by para-toluenesulfonic acid (p-TSA) to form substituted furans is reported. The reaction proceeds under mild conditions at room temperature in methanol to...

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Pd‐Catalyzed Activation of Carbon–Carbon Bonds in Hydroxymethylfurfural Derivatives

Ghahramani,

Meyer,

Unone

et al. 2023

Chemistry A European J

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Palladium‐catalyzed activation of C–C bonds in organic molecules is a powerful tool for the synthesis of value‐added compounds. 5‐Hydroxymethylfurfural (HMF) derivatives are a promising class of biomass‐derived chemicals that have received considerable attention due to their potential applications in the synthesis of biologically active molecules and materials. However, the selective activation of unstrained C–C bonds is a challenging task, mainly due to their relatively high bond dissociation energies. Herein, we report a palladium‐catalyzed method for the efficient C–C bond activation of HMF derivatives, enabling their arylation with iodobenzenes. Mechanistic studies, including reaction‐profile analysis, competition experiments and head‐space IR‐spectroscopy suggest a decarboxylative mechanism.

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Pd‐Catalyzed Activation of Carbon–Carbon Bonds in Hydroxymethylfurfural Derivatives

Ghahramani,

Meyer,

Unone

et al. 2023

Chemistry A European J

View full text Add to dashboard Cite

show abstract

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Brønsted acid-catalysed desilylative heterocyclisation to form substituted furans

Abstract: Heterocyclisation of tert-butyldimethylsilyl (TBS) protected γ-hydroxy-α,β-unsaturated ketones catalysed by para-toluenesulfonic acid (p-TSA) to form substituted furans is reported. The reaction proceeds under mild conditions at room temperature in methanol to...

Cited by 1 publication

References 49 publications

Pd‐Catalyzed Activation of Carbon–Carbon Bonds in Hydroxymethylfurfural Derivatives

Pd‐Catalyzed Activation of Carbon–Carbon Bonds in Hydroxymethylfurfural Derivatives

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