Visible-Light-Induced Glycosylation/Annulation of 2-Isocyanobiaryls and Glycosyl NHP Esters to Access Nonclassical Heteroaryl C-Glycosides

Visible-Light-Induced Glycosylation/Annulation of 2-Isocyanobiaryls and Glycosyl NHP Esters to Access Nonclassical Heteroaryl C-Glycosides

A photoredox-promoted cascade glycosylation/cyclization reaction of 2-isocyanobiaryls and glycosyl NHP esters was established for the synthesis of nonclassical heteroaryl C-glycosides. This methodology is characterized by an exceedingly simple reaction system, high diastereoselectivity, and good fun...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2025-01
Hauptverfasser: Lv, Guanghui, Wang, Yangyang, Zhang, Penghua, Zhu, Yafei, Wang, Mi, Ma, Zhaohui, Zhang, Cuimei, Chen, Jian, Guo, Li, Wu, Yong
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 Journal of organic chemistry
container_volume
creator Lv, Guanghui
Wang, Yangyang
Zhang, Penghua
Zhu, Yafei
Wang, Mi
Ma, Zhaohui
Zhang, Cuimei
Chen, Jian
Guo, Li
Wu, Yong
description A photoredox-promoted cascade glycosylation/cyclization reaction of 2-isocyanobiaryls and glycosyl NHP esters was established for the synthesis of nonclassical heteroaryl C-glycosides. This methodology is characterized by an exceedingly simple reaction system, high diastereoselectivity, and good functional group tolerance. In contrast to traditional strategies, this innovative approach circumvents the need for high temperature, transition metal, and photocatalyst, offering an environmentally friendly and efficient protocol.
doi_str_mv 10.1021/acs.joc.4c02528
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_3155357769</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3155357769</sourcerecordid><originalsourceid>FETCH-LOGICAL-c969-211cb23f46a3e921fe1947538fca4790b3f6865ed90f8ffdb48eac1c72653d9c3</originalsourceid><addsrcrecordid>eNpFkD1PwzAQhi0EgvIxsyGPLG79ESfxWFXQVqqAAbFGzsUGIzeGXDL0L_CrCWqBW-6ke99Xdw8h14JPBZdiZgGn7wmmGXCpZXlEJkJLznLDs2My4VxKpmSuzsg54jsfS2t9Ss6UKXlWaDMhXy8BQx0d24TXt56t22YA19Bl3EHCXbR9SO1s3rbDfqTJU8nWmGBn21QH2-0iUtv-O-jD6oneYe86pH2icwCHSB9SC9EiBrCRrty4TT9WumB7X2gcXpITbyO6q0O_IM_3d8-LFds8LteL-YaByQ2TQkAtlc9yq5yRwjthxldU6cFmheG18nmZa9cY7kvvmzornQUBhcy1agyoC3K7j_3o0ufgsK-2AcHFaFuXBqyU0FrposjNKJ3tpdAlxM756qML2_HwSvDqh3818q9G_tWB_-i4OYQP9dY1f_pf4Oob4QmE0w</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>3155357769</pqid></control><display><type>article</type><title>Visible-Light-Induced Glycosylation/Annulation of 2-Isocyanobiaryls and Glycosyl NHP Esters to Access Nonclassical Heteroaryl C-Glycosides</title><source>American Chemical Society Journals</source><creator>Lv, Guanghui ; Wang, Yangyang ; Zhang, Penghua ; Zhu, Yafei ; Wang, Mi ; Ma, Zhaohui ; Zhang, Cuimei ; Chen, Jian ; Guo, Li ; Wu, Yong</creator><creatorcontrib>Lv, Guanghui ; Wang, Yangyang ; Zhang, Penghua ; Zhu, Yafei ; Wang, Mi ; Ma, Zhaohui ; Zhang, Cuimei ; Chen, Jian ; Guo, Li ; Wu, Yong</creatorcontrib><description>A photoredox-promoted cascade glycosylation/cyclization reaction of 2-isocyanobiaryls and glycosyl NHP esters was established for the synthesis of nonclassical heteroaryl C-glycosides. This methodology is characterized by an exceedingly simple reaction system, high diastereoselectivity, and good functional group tolerance. In contrast to traditional strategies, this innovative approach circumvents the need for high temperature, transition metal, and photocatalyst, offering an environmentally friendly and efficient protocol.</description><identifier>ISSN: 0022-3263</identifier><identifier>ISSN: 1520-6904</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.4c02528</identifier><identifier>PMID: 39804759</identifier><language>eng</language><publisher>United States</publisher><ispartof>Journal of organic chemistry, 2025-01</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c969-211cb23f46a3e921fe1947538fca4790b3f6865ed90f8ffdb48eac1c72653d9c3</cites><orcidid>0000-0003-0719-4963</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/39804759$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lv, Guanghui</creatorcontrib><creatorcontrib>Wang, Yangyang</creatorcontrib><creatorcontrib>Zhang, Penghua</creatorcontrib><creatorcontrib>Zhu, Yafei</creatorcontrib><creatorcontrib>Wang, Mi</creatorcontrib><creatorcontrib>Ma, Zhaohui</creatorcontrib><creatorcontrib>Zhang, Cuimei</creatorcontrib><creatorcontrib>Chen, Jian</creatorcontrib><creatorcontrib>Guo, Li</creatorcontrib><creatorcontrib>Wu, Yong</creatorcontrib><title>Visible-Light-Induced Glycosylation/Annulation of 2-Isocyanobiaryls and Glycosyl NHP Esters to Access Nonclassical Heteroaryl C-Glycosides</title><title>Journal of organic chemistry</title><addtitle>J Org Chem</addtitle><description>A photoredox-promoted cascade glycosylation/cyclization reaction of 2-isocyanobiaryls and glycosyl NHP esters was established for the synthesis of nonclassical heteroaryl C-glycosides. This methodology is characterized by an exceedingly simple reaction system, high diastereoselectivity, and good functional group tolerance. In contrast to traditional strategies, this innovative approach circumvents the need for high temperature, transition metal, and photocatalyst, offering an environmentally friendly and efficient protocol.</description><issn>0022-3263</issn><issn>1520-6904</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2025</creationdate><recordtype>article</recordtype><recordid>eNpFkD1PwzAQhi0EgvIxsyGPLG79ESfxWFXQVqqAAbFGzsUGIzeGXDL0L_CrCWqBW-6ke99Xdw8h14JPBZdiZgGn7wmmGXCpZXlEJkJLznLDs2My4VxKpmSuzsg54jsfS2t9Ss6UKXlWaDMhXy8BQx0d24TXt56t22YA19Bl3EHCXbR9SO1s3rbDfqTJU8nWmGBn21QH2-0iUtv-O-jD6oneYe86pH2icwCHSB9SC9EiBrCRrty4TT9WumB7X2gcXpITbyO6q0O_IM_3d8-LFds8LteL-YaByQ2TQkAtlc9yq5yRwjthxldU6cFmheG18nmZa9cY7kvvmzornQUBhcy1agyoC3K7j_3o0ufgsK-2AcHFaFuXBqyU0FrposjNKJ3tpdAlxM756qML2_HwSvDqh3818q9G_tWB_-i4OYQP9dY1f_pf4Oob4QmE0w</recordid><startdate>20250113</startdate><enddate>20250113</enddate><creator>Lv, Guanghui</creator><creator>Wang, Yangyang</creator><creator>Zhang, Penghua</creator><creator>Zhu, Yafei</creator><creator>Wang, Mi</creator><creator>Ma, Zhaohui</creator><creator>Zhang, Cuimei</creator><creator>Chen, Jian</creator><creator>Guo, Li</creator><creator>Wu, Yong</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-0719-4963</orcidid></search><sort><creationdate>20250113</creationdate><title>Visible-Light-Induced Glycosylation/Annulation of 2-Isocyanobiaryls and Glycosyl NHP Esters to Access Nonclassical Heteroaryl C-Glycosides</title><author>Lv, Guanghui ; Wang, Yangyang ; Zhang, Penghua ; Zhu, Yafei ; Wang, Mi ; Ma, Zhaohui ; Zhang, Cuimei ; Chen, Jian ; Guo, Li ; Wu, Yong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c969-211cb23f46a3e921fe1947538fca4790b3f6865ed90f8ffdb48eac1c72653d9c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2025</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lv, Guanghui</creatorcontrib><creatorcontrib>Wang, Yangyang</creatorcontrib><creatorcontrib>Zhang, Penghua</creatorcontrib><creatorcontrib>Zhu, Yafei</creatorcontrib><creatorcontrib>Wang, Mi</creatorcontrib><creatorcontrib>Ma, Zhaohui</creatorcontrib><creatorcontrib>Zhang, Cuimei</creatorcontrib><creatorcontrib>Chen, Jian</creatorcontrib><creatorcontrib>Guo, Li</creatorcontrib><creatorcontrib>Wu, Yong</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lv, Guanghui</au><au>Wang, Yangyang</au><au>Zhang, Penghua</au><au>Zhu, Yafei</au><au>Wang, Mi</au><au>Ma, Zhaohui</au><au>Zhang, Cuimei</au><au>Chen, Jian</au><au>Guo, Li</au><au>Wu, Yong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Visible-Light-Induced Glycosylation/Annulation of 2-Isocyanobiaryls and Glycosyl NHP Esters to Access Nonclassical Heteroaryl C-Glycosides</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J Org Chem</addtitle><date>2025-01-13</date><risdate>2025</risdate><issn>0022-3263</issn><issn>1520-6904</issn><eissn>1520-6904</eissn><abstract>A photoredox-promoted cascade glycosylation/cyclization reaction of 2-isocyanobiaryls and glycosyl NHP esters was established for the synthesis of nonclassical heteroaryl C-glycosides. This methodology is characterized by an exceedingly simple reaction system, high diastereoselectivity, and good functional group tolerance. In contrast to traditional strategies, this innovative approach circumvents the need for high temperature, transition metal, and photocatalyst, offering an environmentally friendly and efficient protocol.</abstract><cop>United States</cop><pmid>39804759</pmid><doi>10.1021/acs.joc.4c02528</doi><orcidid>https://orcid.org/0000-0003-0719-4963</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2025-01
issn 0022-3263
1520-6904
1520-6904
language eng
recordid cdi_proquest_miscellaneous_3155357769
source American Chemical Society Journals
title Visible-Light-Induced Glycosylation/Annulation of 2-Isocyanobiaryls and Glycosyl NHP Esters to Access Nonclassical Heteroaryl C-Glycosides
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-28T23%3A33%3A28IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Visible-Light-Induced%20Glycosylation/Annulation%20of%202-Isocyanobiaryls%20and%20Glycosyl%20NHP%20Esters%20to%20Access%20Nonclassical%20Heteroaryl%20C-Glycosides&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Lv,%20Guanghui&rft.date=2025-01-13&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.4c02528&rft_dat=%3Cproquest_cross%3E3155357769%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=3155357769&rft_id=info:pmid/39804759&rfr_iscdi=true