Friedel-Crafts Acylation for Accessing Multi-Bridge-Functionalized Large Pillar[n]arenes
© 2023 Wiley-VCH GmbH..
Pillar[n]arenes can be constructed using a Friedel-Crafts alkylation process. However, due to the reversible nature of the alkylation, mixture of large pillar[n]arenes (n≥7) are obtained as minor products, and thus laborious purification are necessary to isolate the larger pillar[n]arenes. Moreover, inert methylene bridges are introduced during the alkylation process, and the multi-functionalization of the bridges has never been investigated. Herein, an irreversible Friedel-Crafts acylation is used to prepare pillar[n]arenes. Due to the irreversible nature of the acylation, the reaction of precursors bearing carboxylic acids and electron-rich arene rings results in a size-exclusive formation of pillar[n]arenes, in which the ring-size is determined by the precursor length. Because of this size-selective formation, laborious separation of undesired macrocycles is not necessary. Moreover, the bridges of pillar[n]arenes are selectively installed with reactive carbonyl groups using the acylation method, whose positions are determined by the precursor used. The carbonyl bridges can be easily converted into versatile functional groups, leading to various laterally modified pillar[n]arenes, which cannot be accessed by the alkylation strategy.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2024 |
|---|---|
| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:63 |
|---|---|
| Enthalten in: |
Angewandte Chemie (International ed. in English) - 63(2024), 6 vom: 05. Feb., Seite e202318268 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Shi, Tan-Hao [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
Friedel-Crafts Reaction |
|---|
| Anmerkungen: |
Date Revised 01.02.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
|---|
| doi: |
10.1002/anie.202318268 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM365992941 |
|---|
| LEADER | 01000caa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM365992941 | ||
| 003 | DE-627 | ||
| 005 | 20240201232049.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 231227s2024 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1002/anie.202318268 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n1277.xml |
| 035 | |a (DE-627)NLM365992941 | ||
| 035 | |a (NLM)38108597 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Shi, Tan-Hao |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Friedel-Crafts Acylation for Accessing Multi-Bridge-Functionalized Large Pillar[n]arenes |
| 264 | 1 | |c 2024 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Revised 01.02.2024 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a © 2023 Wiley-VCH GmbH. | ||
| 520 | |a Pillar[n]arenes can be constructed using a Friedel-Crafts alkylation process. However, due to the reversible nature of the alkylation, mixture of large pillar[n]arenes (n≥7) are obtained as minor products, and thus laborious purification are necessary to isolate the larger pillar[n]arenes. Moreover, inert methylene bridges are introduced during the alkylation process, and the multi-functionalization of the bridges has never been investigated. Herein, an irreversible Friedel-Crafts acylation is used to prepare pillar[n]arenes. Due to the irreversible nature of the acylation, the reaction of precursors bearing carboxylic acids and electron-rich arene rings results in a size-exclusive formation of pillar[n]arenes, in which the ring-size is determined by the precursor length. Because of this size-selective formation, laborious separation of undesired macrocycles is not necessary. Moreover, the bridges of pillar[n]arenes are selectively installed with reactive carbonyl groups using the acylation method, whose positions are determined by the precursor used. The carbonyl bridges can be easily converted into versatile functional groups, leading to various laterally modified pillar[n]arenes, which cannot be accessed by the alkylation strategy | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Friedel-Crafts Reaction | |
| 650 | 4 | |a Macrocycles | |
| 650 | 4 | |a Pillar[n]arenes | |
| 650 | 4 | |a Supramolecular Chemistry | |
| 700 | 1 | |a Akine, Shigehisa |e verfasserin |4 aut | |
| 700 | 1 | |a Ohtani, Shunsuke |e verfasserin |4 aut | |
| 700 | 1 | |a Kato, Kenichi |e verfasserin |4 aut | |
| 700 | 1 | |a Ogoshi, Tomoki |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Angewandte Chemie (International ed. in English) |d 1964 |g 63(2024), 6 vom: 05. Feb., Seite e202318268 |w (DE-627)NLM000105422 |x 1521-3773 |7 nnns |
| 773 | 1 | 8 | |g volume:63 |g year:2024 |g number:6 |g day:05 |g month:02 |g pages:e202318268 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1002/anie.202318268 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 63 |j 2024 |e 6 |b 05 |c 02 |h e202318268 | ||