The rapid synthesis of π-extended azacorannulenes
In this account we describe our recent development of rapid syntheses of π-extended azacorannulenes. The key to successful synthesis is the use of polycyclic aromatic azomethine ylides, which exhibit extremely high reactivity in sequential 1,3-dipolar cycloadditions with alkenes and alkynes followed...
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| Format: | Article |
| Language: | English |
| Published: |
2022
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| Online Access: | https://hdl.handle.net/10356/161294 |
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| Institution: | Nanyang Technological University |
| Language: | English |
| Summary: | In this account we describe our recent development of rapid syntheses of π-extended azacorannulenes. The key to successful synthesis is the use of polycyclic aromatic azomethine ylides, which exhibit extremely high reactivity in sequential 1,3-dipolar cycloadditions with alkenes and alkynes followed by oxidation to form fused pyrroles. This efficient construction of the polycyclic pyrrole structure has led to the rapid synthesis of various π-extended azacorannulenes, which are characterized by their extended π-surface and highly curved, bowl-shaped structures. The present study provides useful insights toward the bottom-up synthesis and property elucidation of heteroatom-containing fullerenes and their fragment molecules. |
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