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Domino Aryne Annulation via a Nucleophilic-Ene Process
Hai Xu1, Jia He1, Jiarong Shi1
1School of Chemistry and Chemical Engineering , Chongqing University , 174 Shazheng Street , Chongqing 400030 , P. R. China.
Journal of the American Chemical Society
|February 10, 2018
Summary
This study introduces a novel domino aryne annulation method using 1,2-benzdiyne equivalents. This transition metal-free approach efficiently synthesizes diverse benzo-fused N-heterocyclic frameworks.
Area of Science:
- Organic Chemistry
- Synthetic Methodology
- Heterocyclic Chemistry
Background:
- 1,2-Benzdiyne equivalents are known to react with two arynophiles.
- Iterative generation of 1,2- and 2,3-aryne intermediates enables complex transformations.
- Developing efficient and versatile synthetic routes to N-heterocycles is crucial.
Purpose of the Study:
- To develop a novel domino aryne annulation approach.
- To achieve synthesis of benzo-fused N-heterocyclic frameworks.
- To explore the scope and limitations of the new methodology.
Main Methods:
- Rational modification of the second leaving group on aryne precursors.
- Utilizing a nucleophilic-ene reaction sequence.
- Employing transition metal-free conditions.
Main Results:
- A domino aryne annulation strategy was successfully developed.
- Various benzo-fused N-heterocyclic frameworks were synthesized.
- The method demonstrated a broad substrate scope.
Conclusions:
- The developed domino aryne annulation is an efficient method for constructing N-heterocycles.
- Transition metal-free conditions offer advantages in terms of sustainability and cost.
- This approach expands the synthetic toolkit for heterocyclic chemistry.
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