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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sg-ntu-dr.10356-1612942022-08-24T03:04:29Z The rapid synthesis of π-extended azacorannulenes Ito, Shingo School of Physical and Mathematical Sciences Science::Chemistry 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. Ministry of Education (MOE) Nanyang Technological University This work was supported by JSPS KAKENHI, including Grant─ in─ Aids for Young Scientists (A) (No. 16H06030) and Challenging Exploratory Research (No. 24655096), and Nanyang Technological University and the Singapore Ministry of Education via Academic Research Fund Tier 1: 2018─ T1─ 002─ 021. The nancial support of the Yazaki Memorial Foundation for Science and Technology is greatly appreciated. 2022-08-24T03:04:28Z 2022-08-24T03:04:28Z 2019 Journal Article Ito, S. (2019). The rapid synthesis of π-extended azacorannulenes. Journal of Synthetic Organic Chemistry, 77(11), 1128-1135. https://dx.doi.org/10.5059/yukigoseikyokaishi.77.1128 0037-9980 https://hdl.handle.net/10356/161294 10.5059/yukigoseikyokaishi.77.1128 2-s2.0-85084929407 11 77 1128 1135 en 2018─ T1─ 002─ 021 Journal of Synthetic Organic Chemistry © 2019 The Society of Synthetic Organic Chemistry, Japan. All rights reserved. |
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Science::Chemistry Ito, Shingo The rapid synthesis of π-extended azacorannulenes |
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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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School of Physical and Mathematical Sciences |
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School of Physical and Mathematical Sciences Ito, Shingo |
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Article |
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Ito, Shingo |
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Ito, Shingo |
title |
The rapid synthesis of π-extended azacorannulenes |
title_short |
The rapid synthesis of π-extended azacorannulenes |
title_full |
The rapid synthesis of π-extended azacorannulenes |
title_fullStr |
The rapid synthesis of π-extended azacorannulenes |
title_full_unstemmed |
The rapid synthesis of π-extended azacorannulenes |
title_sort |
rapid synthesis of π-extended azacorannulenes |
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2022 |
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https://hdl.handle.net/10356/161294 |
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