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Synthesis 2021; 53(04): 636-652
DOI: 10.1055/s-0040-1707327
DOI: 10.1055/s-0040-1707327
short review
Recent Progress towards Organocatalyzed Asymmetric (Hetero)Arene Formation
We acknowledge financial support from the ‘1000-Youth Talents Program’ and are grateful to Sun Yat-Sen University for providing a young teacher research grant.
Abstract
Owing to the importance of arene moieties in organic chemistry, methods for arene construction attract great attention. Besides the traditional substitution strategy from pre-existing arenes, the straightforward formation of arene cores can also provide significant shortcuts towards a wide array of target molecules with different substitution patterns. Among direct arene formation reactions, applying environmentally benign organocatalysis to access arene moieties continues to attract increasing attention. This short review provides a brief summary of recent progress on organocatalyzed de novo (hetero)arene formation and applications in enantioselective synthesis.
1 Introduction
2 Arene Formation with Non-Covalent Organocatalysts
2.1 Arene Formation with Acid Organocatalysts
2.2 Arene Formation with Base Organocatalysts
2.3 Arene Formation with Hydrogen-Bonding Organocatalysts
3 Arene Formation with Covalent Organocatalysts
3.1 Arene Formation with Lewis Base Organocatalysts
3.1.1 Arene Formation with Secondary Amine Organocatalysts
3.1.2 Arene Formation with Tertiary Amine, Tertiary Phosphine and Sulfide Organocatalysts
3.1.3 Arene Formation with N-Heterocyclic Carbene Organocatalysts
3.2 Arene Formation with Lewis Acid Organocatalysts
4 Conclusion
Key words
(hetero)arene formation - organocatalysis - benzannulation - desymmetrization - axial chiralityPublication History
Received: 30 August 2020
Accepted after revision: 15 September 2020
Article published online:
28 October 2020
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For reviews on the synthesis of heteroarenes, see:
Selected examples: