Formamide Catalysis Facilitates the Transformation of Aldehydes into Geminal Dichlorides

Peter Helmut Huy

doi:10.1055/s-0037-1611798

Synthesis, Table of Contents

Synthesis 2019; 51(12): 2474-2483
DOI: 10.1055/s-0037-1611798

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Formamide Catalysis Facilitates the Transformation of Aldehydes into Geminal Dichlorides

Peter Helmut Huy *

Saarland University, Institute of Organic Chemistry, P. O. Box 151150, 66041 Saarbruecken, Germany Email: peter.huy@uni-saarland.de

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Abstract

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Abstract

Herein, a novel method for the transformation of aldehydes into geminal dichlorides based on phthaloyl chloride as reagent and N-formylpyrrolidine as Lewis base catalyst is disclosed. Given the mild reaction conditions, the current protocol is distinguished by high levels of functional group compatibility and scalability and is operationally simple. The in situ formation of a Vilsmeier Haack reagent type intermediate is likely to be essential for this organocatalytic nucleophilic substitution reaction.

Key words

homogeneous catalysis - nucleophilic substitutions - Lewis base catalysis - halogenation - organocatalysis - geminal dihalogenides - Vilsmeier Haack reagent

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References

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18 It is recommended that toluene is removed before the adsorption on silica gel. If SiO₂ is added after the transfer of the reaction mixture to a 25 mL flask, the residue obtained after evaporation of the solvent is less fine-powdered and stickier.
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