Domino Reactions with Dicyanoalkenes and Fluorinated Conjugated Sulfinyl Imines. A Convenient Strategy for the Generation of Structural Diversity

Dicyanoalkenes are versatile reagents in organic synthesis and they have been extensively used in a wide variety of organic transformations. However, their reactivity towards fluorinated imines remained almost unnoticed. The divergent reactivity of fluorinated conjugated sulfinyl imines with dicyano...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2024-02, Vol.366 (4), p.970-981
Main Authors: Gaviña, Daniel, Escolano, Marcos, Sotorríos, Lía, Gómez‐Bengoa, Enrique, López‐Ortiz, Fernando, Sánchez‐Roselló, María, Pozo, Carlos
Format: Article
Language:English
Subjects:
Aromatic compounds
Cascade chemical reactions
conjugated fluorinated sulfinyl imines
dicyanoalkenes
divergent reactivity
domino reactions
Fluorination
Imines
Reaction intermediates
Reagents
Rendering
trifluoromethylarenes
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Summary:Dicyanoalkenes are versatile reagents in organic synthesis and they have been extensively used in a wide variety of organic transformations. However, their reactivity towards fluorinated imines remained almost unnoticed. The divergent reactivity of fluorinated conjugated sulfinyl imines with dicyanoalkenes is described herein. On the one hand, when tert‐butyl sulfinyl imines were employed, a cycloaromatization cascade process took place preferentially, rendering valuable trifluoromethyl arenes. On the other hand, the reaction with p‐tolyl sulfinyl imines mainly led to a complex tetracyclic skeleton, involving an azetidinimine rearrangement of a reaction intermediate. Finally, when 1‐indanone‐derived dicyanoalkenes were employed, the aromatization process was interrupted, rendering a new family of diene derivatives. Theoretical calculations were performed in order to shed light on the mechanistic outcome of this transformation.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202301123