Novel Selective Approach to Terminally Substituted [n]Dendralenes

Dendralenes are simple alkenes with cross‐conjugated double bonds that are frequently synthesized due to being potentially valuable building blocks for the synthesis of more complex structures. The synthetic approaches to dendralenes are based on the cross‐coupling reactions of electrophilic and nuc...

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Bibliographic Details
Published in:European journal of organic chemistry 2019-02, Vol.2019 (5), p.957-968
Main Authors: Polák, Peter, Tobrman, Tomáš
Format: Article
Language:English
Subjects:
Alkenes
Aluminum
Chemical reactions
Cross‐coupling
C–C bond formation
Dienes
Electrocyclic reactions
Substitutes
Synthesis
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Summary:Dendralenes are simple alkenes with cross‐conjugated double bonds that are frequently synthesized due to being potentially valuable building blocks for the synthesis of more complex structures. The synthetic approaches to dendralenes are based on the cross‐coupling reactions of electrophilic and nucleophilic synthons derived from geminally substituted ethylene. Our novel methodology for the synthesis of only terminally substituted [3]‐ and [4]dendralenes, as well as 2,3‐disubstituted buta‐1,3‐dienes, involves the preparation of 1,2‐disubstituted cyclobutenes from readily available 2‐bromocyclobutanone and the subsequent thermal ring‐opening reactions. A methodology for the synthesis of terminally substituted [3]‐ and [4]dendralenes, as well as 2,3‐disubstituted buta‐1,3‐dienes has been prepared. This involves the preparation of 1,2‐disubstituted cyclobutenes from readily available 2‐bromocyclobutanone and the subsequent thermal ring‐opening reactions.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201801522