Paraformaldehyde

Taylor, Richard T.; O’Sullivan, Theresa J.

doi:10.1002/047084289x.rp018.pub2

Encyclopedia of Reagents for Organic Synthesis 2008

DOI: 10.1002/047084289x.rp018.pub2

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Paraformaldehyde

Richard T. Taylor

Theresa J. O’Sullivan

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2013

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“…Formaldehyde, a basic building block in chemical synthesis, is commonly used as a one-carbon electrophile . With N -heterocyclic carbenes (NHCs) as the catalysts, , through polarity inversion, formaldehyde can be activated to generate an acyl anion intermediate as a one-carbon nucleophile.…”

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confidence: 99%

Catalytic Activation of Carbohydrates as Formaldehyde Equivalents for Stetter Reaction with Enones

et al. 2013

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We disclose the first catalytic activation of carbohydrates as formaldehyde equivalents to generate acyl anions as one-carbon nucleophilic units for a Stetter reaction. The activation involves N-heterocyclic carbene (NHC)-catalyzed C-C bond cleavage of carbohydrates via a retro-benzoin-type process to generate the acyl anion intermediates. This Stetter reaction constitutes the first success in generating formal formaldehyde-derived acyl anions as one-carbon nucleophiles for non-self-benzoin processes. The renewable nature of carbohydrates, accessible from biomass, further highlights the practical potential of this fundamentally interesting catalytic activation.

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Catalytic Activation of Carbohydrates as Formaldehyde Equivalents for Stetter Reaction with Enones

et al. 2013

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Paraformaldehyde

Cited by 1 publication

References 43 publications

Catalytic Activation of Carbohydrates as Formaldehyde Equivalents for Stetter Reaction with Enones

Catalytic Activation of Carbohydrates as Formaldehyde Equivalents for Stetter Reaction with Enones

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