Sulfoximines Assisted Rh(III)-Catalyzed C–H Activation/Annulation Cascade to Synthesize Highly Fused Indeno-1,2-benzothiazines

A facile access to highly fused tetracyclic indeno-1,2-benzothiazines has been established via a Rh­(III)-catalyzed C–H bond activation and intramolecular annulation cascade between sulfoximides and all-carbon diazo indandiones. This strategy is characterized by the fact that the diazo coupling part...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2021-11, Vol.86 (21), p.15217-15227
Hauptverfasser: Li, Jian, Li, Hui, Fang, Daqing, Liu, Lingjun, Han, Xu, Sun, Jina, Li, Chunpu, Zhou, Yu, Ye, Deju, Liu, Hong
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 15227
container_issue 21
container_start_page 15217
container_title Journal of organic chemistry
container_volume 86
creator Li, Jian
Li, Hui
Fang, Daqing
Liu, Lingjun
Han, Xu
Sun, Jina
Li, Chunpu
Zhou, Yu
Ye, Deju
Liu, Hong
description A facile access to highly fused tetracyclic indeno-1,2-benzothiazines has been established via a Rh­(III)-catalyzed C–H bond activation and intramolecular annulation cascade between sulfoximides and all-carbon diazo indandiones. This strategy is characterized by the fact that the diazo coupling partners do not require preactivation, along with its high efficiency, broad substrate generality, and facile transformation. Particularly, the highly conjugated tetracyclic products demonstrate good optical properties and can easily enter cells to emit bright fluorescence for live cell imaging.
doi_str_mv 10.1021/acs.joc.1c01820
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2580017911</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2580017911</sourcerecordid><originalsourceid>FETCH-LOGICAL-a333t-8e3747968c9582afdde69babad5b35110671910e04da79c3d2a14dfaa805efa63</originalsourceid><addsrcrecordid>eNp1kMtO3DAUhi3Uqgy0a3ZVliDIjC9xLstRVJhISJVKu45O7JOOUcamsYOYWfEOfUOeBNOZdldvjnX0_b_lj5AzRueMcrYA5ef3Ts2Zoqzk9IjMmOQ0zSuavSMzSjlPBc_FMTnx_p7GI6X8QI5FljNRiGpGnu-moXdPZmMs-mTpvfEBdfJtfd40zUVaQ4Bhu4ub-uX59ypZqmAeIRhnF0trp-HPNanBK9CYBJfcbW1Yozc7TFbm53rYJteTj_HGarQuZVc87dDuXFgb2L29-ZG872Hw-OkwT8mP6y_f61V6-_WmqZe3KQghQlqiKLKiyktVyZJDrzXmVQcdaNkJyRjNC1YxijTTUFRKaA4s0z1ASSX2kItTcr7vfRjdrwl9aDfGKxwGsOgm33JZUsqKirGILvaoGp33I_btw2g2MG5bRts37W3U3kbt7UF7THw-lE_dBvU__q_nCFzugX1yGm3863_rXgEG-49f</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2580017911</pqid></control><display><type>article</type><title>Sulfoximines Assisted Rh(III)-Catalyzed C–H Activation/Annulation Cascade to Synthesize Highly Fused Indeno-1,2-benzothiazines</title><source>ACS Publications</source><source>MEDLINE</source><creator>Li, Jian ; Li, Hui ; Fang, Daqing ; Liu, Lingjun ; Han, Xu ; Sun, Jina ; Li, Chunpu ; Zhou, Yu ; Ye, Deju ; Liu, Hong</creator><creatorcontrib>Li, Jian ; Li, Hui ; Fang, Daqing ; Liu, Lingjun ; Han, Xu ; Sun, Jina ; Li, Chunpu ; Zhou, Yu ; Ye, Deju ; Liu, Hong</creatorcontrib><description>A facile access to highly fused tetracyclic indeno-1,2-benzothiazines has been established via a Rh­(III)-catalyzed C–H bond activation and intramolecular annulation cascade between sulfoximides and all-carbon diazo indandiones. This strategy is characterized by the fact that the diazo coupling partners do not require preactivation, along with its high efficiency, broad substrate generality, and facile transformation. Particularly, the highly conjugated tetracyclic products demonstrate good optical properties and can easily enter cells to emit bright fluorescence for live cell imaging.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.1c01820</identifier><identifier>PMID: 34613739</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Carbon ; Catalysis ; Rhodium</subject><ispartof>Journal of organic chemistry, 2021-11, Vol.86 (21), p.15217-15227</ispartof><rights>2021 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a333t-8e3747968c9582afdde69babad5b35110671910e04da79c3d2a14dfaa805efa63</citedby><cites>FETCH-LOGICAL-a333t-8e3747968c9582afdde69babad5b35110671910e04da79c3d2a14dfaa805efa63</cites><orcidid>0000-0003-3685-6268 ; 0000-0002-7684-2939</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/acs.joc.1c01820$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.1c01820$$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/34613739$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Jian</creatorcontrib><creatorcontrib>Li, Hui</creatorcontrib><creatorcontrib>Fang, Daqing</creatorcontrib><creatorcontrib>Liu, Lingjun</creatorcontrib><creatorcontrib>Han, Xu</creatorcontrib><creatorcontrib>Sun, Jina</creatorcontrib><creatorcontrib>Li, Chunpu</creatorcontrib><creatorcontrib>Zhou, Yu</creatorcontrib><creatorcontrib>Ye, Deju</creatorcontrib><creatorcontrib>Liu, Hong</creatorcontrib><title>Sulfoximines Assisted Rh(III)-Catalyzed C–H Activation/Annulation Cascade to Synthesize Highly Fused Indeno-1,2-benzothiazines</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A facile access to highly fused tetracyclic indeno-1,2-benzothiazines has been established via a Rh­(III)-catalyzed C–H bond activation and intramolecular annulation cascade between sulfoximides and all-carbon diazo indandiones. This strategy is characterized by the fact that the diazo coupling partners do not require preactivation, along with its high efficiency, broad substrate generality, and facile transformation. Particularly, the highly conjugated tetracyclic products demonstrate good optical properties and can easily enter cells to emit bright fluorescence for live cell imaging.</description><subject>Carbon</subject><subject>Catalysis</subject><subject>Rhodium</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kMtO3DAUhi3Uqgy0a3ZVliDIjC9xLstRVJhISJVKu45O7JOOUcamsYOYWfEOfUOeBNOZdldvjnX0_b_lj5AzRueMcrYA5ef3Ts2Zoqzk9IjMmOQ0zSuavSMzSjlPBc_FMTnx_p7GI6X8QI5FljNRiGpGnu-moXdPZmMs-mTpvfEBdfJtfd40zUVaQ4Bhu4ub-uX59ypZqmAeIRhnF0trp-HPNanBK9CYBJfcbW1Yozc7TFbm53rYJteTj_HGarQuZVc87dDuXFgb2L29-ZG872Hw-OkwT8mP6y_f61V6-_WmqZe3KQghQlqiKLKiyktVyZJDrzXmVQcdaNkJyRjNC1YxijTTUFRKaA4s0z1ASSX2kItTcr7vfRjdrwl9aDfGKxwGsOgm33JZUsqKirGILvaoGp33I_btw2g2MG5bRts37W3U3kbt7UF7THw-lE_dBvU__q_nCFzugX1yGm3863_rXgEG-49f</recordid><startdate>20211105</startdate><enddate>20211105</enddate><creator>Li, Jian</creator><creator>Li, Hui</creator><creator>Fang, Daqing</creator><creator>Liu, Lingjun</creator><creator>Han, Xu</creator><creator>Sun, Jina</creator><creator>Li, Chunpu</creator><creator>Zhou, Yu</creator><creator>Ye, Deju</creator><creator>Liu, Hong</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-3685-6268</orcidid><orcidid>https://orcid.org/0000-0002-7684-2939</orcidid></search><sort><creationdate>20211105</creationdate><title>Sulfoximines Assisted Rh(III)-Catalyzed C–H Activation/Annulation Cascade to Synthesize Highly Fused Indeno-1,2-benzothiazines</title><author>Li, Jian ; Li, Hui ; Fang, Daqing ; Liu, Lingjun ; Han, Xu ; Sun, Jina ; Li, Chunpu ; Zhou, Yu ; Ye, Deju ; Liu, Hong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a333t-8e3747968c9582afdde69babad5b35110671910e04da79c3d2a14dfaa805efa63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Carbon</topic><topic>Catalysis</topic><topic>Rhodium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Jian</creatorcontrib><creatorcontrib>Li, Hui</creatorcontrib><creatorcontrib>Fang, Daqing</creatorcontrib><creatorcontrib>Liu, Lingjun</creatorcontrib><creatorcontrib>Han, Xu</creatorcontrib><creatorcontrib>Sun, Jina</creatorcontrib><creatorcontrib>Li, Chunpu</creatorcontrib><creatorcontrib>Zhou, Yu</creatorcontrib><creatorcontrib>Ye, Deju</creatorcontrib><creatorcontrib>Liu, Hong</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><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>Li, Jian</au><au>Li, Hui</au><au>Fang, Daqing</au><au>Liu, Lingjun</au><au>Han, Xu</au><au>Sun, Jina</au><au>Li, Chunpu</au><au>Zhou, Yu</au><au>Ye, Deju</au><au>Liu, Hong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Sulfoximines Assisted Rh(III)-Catalyzed C–H Activation/Annulation Cascade to Synthesize Highly Fused Indeno-1,2-benzothiazines</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2021-11-05</date><risdate>2021</risdate><volume>86</volume><issue>21</issue><spage>15217</spage><epage>15227</epage><pages>15217-15227</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A facile access to highly fused tetracyclic indeno-1,2-benzothiazines has been established via a Rh­(III)-catalyzed C–H bond activation and intramolecular annulation cascade between sulfoximides and all-carbon diazo indandiones. This strategy is characterized by the fact that the diazo coupling partners do not require preactivation, along with its high efficiency, broad substrate generality, and facile transformation. Particularly, the highly conjugated tetracyclic products demonstrate good optical properties and can easily enter cells to emit bright fluorescence for live cell imaging.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>34613739</pmid><doi>10.1021/acs.joc.1c01820</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0003-3685-6268</orcidid><orcidid>https://orcid.org/0000-0002-7684-2939</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2021-11, Vol.86 (21), p.15217-15227
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_2580017911
source ACS Publications; MEDLINE
subjects Carbon
Catalysis
Rhodium
title Sulfoximines Assisted Rh(III)-Catalyzed C–H Activation/Annulation Cascade to Synthesize Highly Fused Indeno-1,2-benzothiazines
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-15T20%3A19%3A01IST&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=Sulfoximines%20Assisted%20Rh(III)-Catalyzed%20C%E2%80%93H%20Activation/Annulation%20Cascade%20to%20Synthesize%20Highly%20Fused%20Indeno-1,2-benzothiazines&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Li,%20Jian&rft.date=2021-11-05&rft.volume=86&rft.issue=21&rft.spage=15217&rft.epage=15227&rft.pages=15217-15227&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.1c01820&rft_dat=%3Cproquest_cross%3E2580017911%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=2580017911&rft_id=info:pmid/34613739&rfr_iscdi=true