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Synthesis 2019; 51(12): 2474-2483
DOI: 10.1055/s-0037-1611798
DOI: 10.1055/s-0037-1611798
feature
Formamide Catalysis Facilitates the Transformation of Aldehydes into Geminal Dichlorides
The author thanks the Deutsche Forschungsgemeinschaft (DFG) and the Fonds der Chemischen Industrie (Liebig fellowship for P.H.) for generous support.Further Information
Publication History
Received: 12 February 2019
Accepted after revision: 22 March 2019
Publication Date:
16 April 2019 (online)
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 reagentSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611798.
- Supporting Information
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For reviews, see:
For Lewis base catalyzed SN protocols using oxalyl chloride as reagent for the synthesis of alkyl halogenides from alcohols, see:
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Selected examples:
Selected examples:
Selected examples:
Selected examples:
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Reviews on Vilsmeier–Haack reagent:
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