Ortho -Functionalization of Pillar[4]arene[1]benzoquinone Monoxime via Selective 1,4-Addition of Grignard Reagents

Ortho -Functionalization of Pillar[4]arene[1]benzoquinone Monoxime via Selective 1,4-Addition of Grignard Reagents

-functionalization of pillar[ ]arenes has been a formidable challenge, partially due to the fragility of their macrocyclic skeletons. In this concise report, we describe a facile synthetic method for monoarylation/alkylation at the position to the oxime functionality in pillar[4]arene[1]benzoquinone...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2025-01
Hauptverfasser: Xu, Yuxuan, Li, Runmei, Liang, Fengjun, Peng, Xiaolong, Liu, Yahu A, Jia, Fei, Wen, Ke
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page
container_issue
container_start_page
container_title Organic letters
container_volume
creator Xu, Yuxuan
Li, Runmei
Liang, Fengjun
Peng, Xiaolong
Liu, Yahu A
Jia, Fei
Wen, Ke
description -functionalization of pillar[ ]arenes has been a formidable challenge, partially due to the fragility of their macrocyclic skeletons. In this concise report, we describe a facile synthetic method for monoarylation/alkylation at the position to the oxime functionality in pillar[4]arene[1]benzoquinone monoxime ( ) via addition of Grignard reagents. The described method enables the creation of various mono- -alkyl/aryl-substituted pillar[5]arene derivatives that were previously inaccessible.
doi_str_mv 10.1021/acs.orglett.4c04564
format Article
fullrecord <record><control><sourceid>pubmed_cross</sourceid><recordid>TN_cdi_pubmed_primary_39849305</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>39849305</sourcerecordid><originalsourceid>FETCH-LOGICAL-c675-e331ab99d922b44ca35d1d0479dcffa1bb930eea5f5cc7dfa48dc14cfc10ab7a3</originalsourceid><addsrcrecordid>eNo9kF1LwzAUhoMobk5_gSD9AXYmTbKul2O4KUwmursxymlyMiNdMtNu6H69Hfu4Oi8Hnhfeh5B7RruMJuwJVNX1YVliXXeFokL2xAVpM5nwOKUyuTznHm2Rm6r6ppQ1n-yatHjWFxmnsk3CNNRfPopHG6dq6x2Udgf7EHkTvduyhDAXCwjocM4WBbqd_9lY5x1Gb975X7vCaGsh-sQSm4ItRuxRxAOt7alkHOzSQdDRB8ISXV3dkisDZYV3x9shs9HzbPgST6bj1-FgEqteKmPknEGRZTpLkkIIBVxqpqlIM62MAVYUzQBEkEYqlWoDoq8VE8ooRqFIgXcIP9Sq4KsqoMnXwa4g_OWM5nuBeSMwPwrMjwIb6uFArTfFCvWZORnj_z10ctQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Ortho -Functionalization of Pillar[4]arene[1]benzoquinone Monoxime via Selective 1,4-Addition of Grignard Reagents</title><source>ACS Publications</source><creator>Xu, Yuxuan ; Li, Runmei ; Liang, Fengjun ; Peng, Xiaolong ; Liu, Yahu A ; Jia, Fei ; Wen, Ke</creator><creatorcontrib>Xu, Yuxuan ; Li, Runmei ; Liang, Fengjun ; Peng, Xiaolong ; Liu, Yahu A ; Jia, Fei ; Wen, Ke</creatorcontrib><description>-functionalization of pillar[ ]arenes has been a formidable challenge, partially due to the fragility of their macrocyclic skeletons. In this concise report, we describe a facile synthetic method for monoarylation/alkylation at the position to the oxime functionality in pillar[4]arene[1]benzoquinone monoxime ( ) via addition of Grignard reagents. The described method enables the creation of various mono- -alkyl/aryl-substituted pillar[5]arene derivatives that were previously inaccessible.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.4c04564</identifier><identifier>PMID: 39849305</identifier><language>eng</language><publisher>United States</publisher><ispartof>Organic letters, 2025-01</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c675-e331ab99d922b44ca35d1d0479dcffa1bb930eea5f5cc7dfa48dc14cfc10ab7a3</cites><orcidid>0000-0002-9717-4351</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,2752,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/39849305$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Xu, Yuxuan</creatorcontrib><creatorcontrib>Li, Runmei</creatorcontrib><creatorcontrib>Liang, Fengjun</creatorcontrib><creatorcontrib>Peng, Xiaolong</creatorcontrib><creatorcontrib>Liu, Yahu A</creatorcontrib><creatorcontrib>Jia, Fei</creatorcontrib><creatorcontrib>Wen, Ke</creatorcontrib><title>Ortho -Functionalization of Pillar[4]arene[1]benzoquinone Monoxime via Selective 1,4-Addition of Grignard Reagents</title><title>Organic letters</title><addtitle>Org Lett</addtitle><description>-functionalization of pillar[ ]arenes has been a formidable challenge, partially due to the fragility of their macrocyclic skeletons. In this concise report, we describe a facile synthetic method for monoarylation/alkylation at the position to the oxime functionality in pillar[4]arene[1]benzoquinone monoxime ( ) via addition of Grignard reagents. The described method enables the creation of various mono- -alkyl/aryl-substituted pillar[5]arene derivatives that were previously inaccessible.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2025</creationdate><recordtype>article</recordtype><recordid>eNo9kF1LwzAUhoMobk5_gSD9AXYmTbKul2O4KUwmursxymlyMiNdMtNu6H69Hfu4Oi8Hnhfeh5B7RruMJuwJVNX1YVliXXeFokL2xAVpM5nwOKUyuTznHm2Rm6r6ppQ1n-yatHjWFxmnsk3CNNRfPopHG6dq6x2Udgf7EHkTvduyhDAXCwjocM4WBbqd_9lY5x1Gb975X7vCaGsh-sQSm4ItRuxRxAOt7alkHOzSQdDRB8ISXV3dkisDZYV3x9shs9HzbPgST6bj1-FgEqteKmPknEGRZTpLkkIIBVxqpqlIM62MAVYUzQBEkEYqlWoDoq8VE8ooRqFIgXcIP9Sq4KsqoMnXwa4g_OWM5nuBeSMwPwrMjwIb6uFArTfFCvWZORnj_z10ctQ</recordid><startdate>20250123</startdate><enddate>20250123</enddate><creator>Xu, Yuxuan</creator><creator>Li, Runmei</creator><creator>Liang, Fengjun</creator><creator>Peng, Xiaolong</creator><creator>Liu, Yahu A</creator><creator>Jia, Fei</creator><creator>Wen, Ke</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-9717-4351</orcidid></search><sort><creationdate>20250123</creationdate><title>Ortho -Functionalization of Pillar[4]arene[1]benzoquinone Monoxime via Selective 1,4-Addition of Grignard Reagents</title><author>Xu, Yuxuan ; Li, Runmei ; Liang, Fengjun ; Peng, Xiaolong ; Liu, Yahu A ; Jia, Fei ; Wen, Ke</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c675-e331ab99d922b44ca35d1d0479dcffa1bb930eea5f5cc7dfa48dc14cfc10ab7a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2025</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xu, Yuxuan</creatorcontrib><creatorcontrib>Li, Runmei</creatorcontrib><creatorcontrib>Liang, Fengjun</creatorcontrib><creatorcontrib>Peng, Xiaolong</creatorcontrib><creatorcontrib>Liu, Yahu A</creatorcontrib><creatorcontrib>Jia, Fei</creatorcontrib><creatorcontrib>Wen, Ke</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xu, Yuxuan</au><au>Li, Runmei</au><au>Liang, Fengjun</au><au>Peng, Xiaolong</au><au>Liu, Yahu A</au><au>Jia, Fei</au><au>Wen, Ke</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ortho -Functionalization of Pillar[4]arene[1]benzoquinone Monoxime via Selective 1,4-Addition of Grignard Reagents</atitle><jtitle>Organic letters</jtitle><addtitle>Org Lett</addtitle><date>2025-01-23</date><risdate>2025</risdate><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>-functionalization of pillar[ ]arenes has been a formidable challenge, partially due to the fragility of their macrocyclic skeletons. In this concise report, we describe a facile synthetic method for monoarylation/alkylation at the position to the oxime functionality in pillar[4]arene[1]benzoquinone monoxime ( ) via addition of Grignard reagents. The described method enables the creation of various mono- -alkyl/aryl-substituted pillar[5]arene derivatives that were previously inaccessible.</abstract><cop>United States</cop><pmid>39849305</pmid><doi>10.1021/acs.orglett.4c04564</doi><orcidid>https://orcid.org/0000-0002-9717-4351</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2025-01
issn 1523-7060
1523-7052
language eng
recordid cdi_pubmed_primary_39849305
source ACS Publications
title Ortho -Functionalization of Pillar[4]arene[1]benzoquinone Monoxime via Selective 1,4-Addition of Grignard Reagents
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-06T22%3A56%3A34IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-pubmed_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Ortho%20-Functionalization%20of%20Pillar%5B4%5Darene%5B1%5Dbenzoquinone%20Monoxime%20via%20Selective%201,4-Addition%20of%20Grignard%20Reagents&rft.jtitle=Organic%20letters&rft.au=Xu,%20Yuxuan&rft.date=2025-01-23&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.4c04564&rft_dat=%3Cpubmed_cross%3E39849305%3C/pubmed_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/39849305&rfr_iscdi=true