Synthesis 2019; 51(12): 2474-2483
DOI: 10.1055/s-0037-1611798
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© Georg Thieme Verlag Stuttgart · New York

Formamide Catalysis Facilitates the Transformation of Aldehydes into Geminal Dichlorides

Saarland University, Institute of Organic Chemistry, P. O. Box 151150, 66041 Saarbruecken, Germany   eMail: peter.huy@uni-saarland.de
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The author thanks the Deutsche Forschungsgemeinschaft (DFG) and the Fonds der Chemischen Industrie (Liebig fellowship for P.H.) for generous support.
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Publikationsverlauf

Received: 12. Februar 2019

Accepted after revision: 22. März 2019

Publikationsdatum:
16.April 2019 (eFirst)

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.

Supporting Information

 
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