Catalyst‐Controlled Dual Reactivity of Sulfonimidamides: Synthesis of Propargylamines and N‐Propargyl Sulfonimidamides

Sulfonimidamides (SIAs) are acting both as surrogate amines and nucleophiles depending on the reaction conditions to access propargylamines and N‐propargyl SIAs, respectively. The amine part of SIAs has been cleaved in an InCl3‐catalyzed three‐component A3 coupling reaction with aldehyde and acetyle...

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Bibliographic Details
Published in:Chemistry : a European journal 2019-01, Vol.25 (3), p.743-749
Main Authors: C. P., Irfana Jesin, Nandi, Ganesh Chandra
Format: Article
Language:English
Subjects:
Acetylene
Alcohols
Amines
Chemical synthesis
Chemistry
Nucleophiles
sulfonimidamides
sulfur
surrogate amine
synthetic methods
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Summary:Sulfonimidamides (SIAs) are acting both as surrogate amines and nucleophiles depending on the reaction conditions to access propargylamines and N‐propargyl SIAs, respectively. The amine part of SIAs has been cleaved in an InCl3‐catalyzed three‐component A3 coupling reaction with aldehyde and acetylene to yield propargylamine. Moreover, N‐propargyl SIAs were obtained via the direct‐imination of propargyl alcohols in the presence of BF3⋅OEt2. A new property of sulfonimidamides was discovered, which is acting as a surrogate amine in an A3 coupling reaction to yield propargylamines. Additionally, propargyl SIAs have also been synthesized via direct‐imination of propargyl alcohols.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201805000