Rim-Differentiated C 5‑Symmetric Tiara-Pillar[5]arenes
The synthesis of “rim-differentiated” C 5-symmetric pillar[5]arenes, whose two rims are decorated with different chemical functionalities, has remained a challenging task. This is due to the inherent statistical nature of the cyclization of 1,4-disubstituted alkoxybenzenes with different substitue...
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| Veröffentlicht in: | Journal of the American Chemical Society 2018-01, Vol.140 (1), p.74-77 |
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| container_title | Journal of the American Chemical Society |
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| creator | Guo, Minjie Wang, Xuemei Zhan, Caihong Demay-Drouhard, Paul Li, Wenjiao Du, Ke Olson, Mark A Zuilhof, Han Sue, Andrew C.-H |
| description | The synthesis of “rim-differentiated” C 5-symmetric pillar[5]arenes, whose two rims are decorated with different chemical functionalities, has remained a challenging task. This is due to the inherent statistical nature of the cyclization of 1,4-disubstituted alkoxybenzenes with different substituents, which leads to four constitutional isomers with only 1/16th being rim-differentiated. Herein, we report a “preoriented” synthetic protocol based on FeCl3-catalyzed cyclization of asymmetrically substituted 2,5-dialkoxybenzyl alcohols. This yields an unprecedented 55% selectivity of the C 5-symmetric tiara-like pillar[5]arene isomer among four constitutional isomers. Based on this new method, a series of functionalizable tiara-pillar[5]arene derivatives with C 5-symmetry was successfully synthesized, isolated, and fully characterized in the solid state. |
| doi_str_mv | 10.1021/jacs.7b10767 |
| format | Article |
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Based on this new method, a series of functionalizable tiara-pillar[5]arene derivatives with C 5-symmetry was successfully synthesized, isolated, and fully characterized in the solid state.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/jacs.7b10767</identifier><identifier>PMID: 29220153</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of the American Chemical Society, 2018-01, Vol.140 (1), p.74-77</ispartof><rights>Copyright © 2017 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a221t-7cb0f0f95c7c956496255f9b28c7525285aad7cb285754a9a55824a526c75adb3</citedby><cites>FETCH-LOGICAL-a221t-7cb0f0f95c7c956496255f9b28c7525285aad7cb285754a9a55824a526c75adb3</cites><orcidid>0000-0003-0398-5063 ; 0000-0001-9557-2658 ; 0000-0001-5773-8506</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jacs.7b10767$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jacs.7b10767$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29220153$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Guo, Minjie</creatorcontrib><creatorcontrib>Wang, Xuemei</creatorcontrib><creatorcontrib>Zhan, Caihong</creatorcontrib><creatorcontrib>Demay-Drouhard, Paul</creatorcontrib><creatorcontrib>Li, Wenjiao</creatorcontrib><creatorcontrib>Du, Ke</creatorcontrib><creatorcontrib>Olson, Mark A</creatorcontrib><creatorcontrib>Zuilhof, Han</creatorcontrib><creatorcontrib>Sue, Andrew C.-H</creatorcontrib><title>Rim-Differentiated C 5‑Symmetric Tiara-Pillar[5]arenes</title><title>Journal of the American Chemical Society</title><addtitle>J. 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Am. Chem. Soc</addtitle><date>2018-01-10</date><risdate>2018</risdate><volume>140</volume><issue>1</issue><spage>74</spage><epage>77</epage><pages>74-77</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>The synthesis of “rim-differentiated” C 5-symmetric pillar[5]arenes, whose two rims are decorated with different chemical functionalities, has remained a challenging task. This is due to the inherent statistical nature of the cyclization of 1,4-disubstituted alkoxybenzenes with different substituents, which leads to four constitutional isomers with only 1/16th being rim-differentiated. Herein, we report a “preoriented” synthetic protocol based on FeCl3-catalyzed cyclization of asymmetrically substituted 2,5-dialkoxybenzyl alcohols. This yields an unprecedented 55% selectivity of the C 5-symmetric tiara-like pillar[5]arene isomer among four constitutional isomers. 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| title | Rim-Differentiated C 5‑Symmetric Tiara-Pillar[5]arenes |
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