Site‐Selective Late‐Stage Aromatic [18F]Fluorination via Aryl Sulfonium Salts
Site‐selective functionalization of C−H bonds in small complex molecules is a long‐standing challenge in organic chemistry. Herein, we report a broadly applicable and site‐selective aromatic C−H dibenzothiophenylation reaction. The conceptual advantage of this transformation is further demonstrated...
Gespeichert in:
| Veröffentlicht in: | Angewandte Chemie International Edition 2020-01, Vol.59 (5), p.1956-1960 |
|---|---|
| Hauptverfasser: | , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1960 |
|---|---|
| container_issue | 5 |
| container_start_page | 1956 |
| container_title | Angewandte Chemie International Edition |
| container_volume | 59 |
| creator | Xu, Peng Zhao, Da Berger, Florian Hamad, Aboubakr Rickmeier, Jens Petzold, Roland Kondratiuk, Mykhailo Bohdan, Kostiantyn Ritter, Tobias |
| description | Site‐selective functionalization of C−H bonds in small complex molecules is a long‐standing challenge in organic chemistry. Herein, we report a broadly applicable and site‐selective aromatic C−H dibenzothiophenylation reaction. The conceptual advantage of this transformation is further demonstrated through the two‐step C−H [18F]fluorination of a series of marketed small‐molecule drugs.
A broadly applicable and site‐selective late‐stage aromatic [18F]fluorination reaction is reported. A collection of three electronically different dibenzothiophenes enables 18F labeling of a series of small complex molecules. |
| doi_str_mv | 10.1002/anie.201912567 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_7004179</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2344218142</sourcerecordid><originalsourceid>FETCH-LOGICAL-c5717-f0bbd3ae7f79e4657a42cb77e9c770c26c1020f8ded66c9c73425c260ffcd7563</originalsourceid><addsrcrecordid>eNqFkctu1DAUhi0EohfYskSR2HSTwbf4JBukUdUplUZUaOiqQpbHOSmunLjYyaDZ8Qg8I0-CqykDZcPK1n8-f_LRT8grRmeMUv7WDA5nnLKG8UrBE3LIKs5KASCe5rsUooS6YgfkKKXbzNc1Vc_JgWCqAcnhkHxcuRF_fv-xQo92dBsslmYXjOYGi3kMvRmdLa5Zvfi88FOIbshBGIqNM3m89cVq8l0Y3NQXK-PH9II864xP-PLhPCZXi7NPp-_L5eX5xel8WdoKGJQdXa9bYRA6aFCqCozkdg2AjQWglivLKKdd3WKrlM2hkLzKMe0620KlxDF5t_PeTeseW4vDGI3Xd9H1Jm51ME4_ngzui74JGw2USgZNFpw8CGL4OmEade-SRe_NgGFKmgvGayoUpxl98w96G6Y45PUyJSVnNZM8U7MdZWNIKWK3_wyj-r4tfd-W3reVH7z-e4U9_rueDDQ74JvzuP2PTs8_XJz9kf8CrNijkw</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2344218142</pqid></control><display><type>article</type><title>Site‐Selective Late‐Stage Aromatic [18F]Fluorination via Aryl Sulfonium Salts</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Xu, Peng ; Zhao, Da ; Berger, Florian ; Hamad, Aboubakr ; Rickmeier, Jens ; Petzold, Roland ; Kondratiuk, Mykhailo ; Bohdan, Kostiantyn ; Ritter, Tobias</creator><creatorcontrib>Xu, Peng ; Zhao, Da ; Berger, Florian ; Hamad, Aboubakr ; Rickmeier, Jens ; Petzold, Roland ; Kondratiuk, Mykhailo ; Bohdan, Kostiantyn ; Ritter, Tobias</creatorcontrib><description>Site‐selective functionalization of C−H bonds in small complex molecules is a long‐standing challenge in organic chemistry. Herein, we report a broadly applicable and site‐selective aromatic C−H dibenzothiophenylation reaction. The conceptual advantage of this transformation is further demonstrated through the two‐step C−H [18F]fluorination of a series of marketed small‐molecule drugs.
A broadly applicable and site‐selective late‐stage aromatic [18F]fluorination reaction is reported. A collection of three electronically different dibenzothiophenes enables 18F labeling of a series of small complex molecules.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201912567</identifier><identifier>PMID: 31697427</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>18F labeling ; Aromatic compounds ; Communication ; Communications ; C−H functionalization ; Fluorination ; late-stage functionalization ; Organic chemistry ; radiochemistry ; Salts ; Sulfonium salts</subject><ispartof>Angewandte Chemie International Edition, 2020-01, Vol.59 (5), p.1956-1960</ispartof><rights>2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</rights><rights>2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5717-f0bbd3ae7f79e4657a42cb77e9c770c26c1020f8ded66c9c73425c260ffcd7563</citedby><cites>FETCH-LOGICAL-c5717-f0bbd3ae7f79e4657a42cb77e9c770c26c1020f8ded66c9c73425c260ffcd7563</cites><orcidid>0000-0002-6957-450X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201912567$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201912567$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,776,780,881,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31697427$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Xu, Peng</creatorcontrib><creatorcontrib>Zhao, Da</creatorcontrib><creatorcontrib>Berger, Florian</creatorcontrib><creatorcontrib>Hamad, Aboubakr</creatorcontrib><creatorcontrib>Rickmeier, Jens</creatorcontrib><creatorcontrib>Petzold, Roland</creatorcontrib><creatorcontrib>Kondratiuk, Mykhailo</creatorcontrib><creatorcontrib>Bohdan, Kostiantyn</creatorcontrib><creatorcontrib>Ritter, Tobias</creatorcontrib><title>Site‐Selective Late‐Stage Aromatic [18F]Fluorination via Aryl Sulfonium Salts</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>Site‐selective functionalization of C−H bonds in small complex molecules is a long‐standing challenge in organic chemistry. Herein, we report a broadly applicable and site‐selective aromatic C−H dibenzothiophenylation reaction. The conceptual advantage of this transformation is further demonstrated through the two‐step C−H [18F]fluorination of a series of marketed small‐molecule drugs.
A broadly applicable and site‐selective late‐stage aromatic [18F]fluorination reaction is reported. A collection of three electronically different dibenzothiophenes enables 18F labeling of a series of small complex molecules.</description><subject>18F labeling</subject><subject>Aromatic compounds</subject><subject>Communication</subject><subject>Communications</subject><subject>C−H functionalization</subject><subject>Fluorination</subject><subject>late-stage functionalization</subject><subject>Organic chemistry</subject><subject>radiochemistry</subject><subject>Salts</subject><subject>Sulfonium salts</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNqFkctu1DAUhi0EohfYskSR2HSTwbf4JBukUdUplUZUaOiqQpbHOSmunLjYyaDZ8Qg8I0-CqykDZcPK1n8-f_LRT8grRmeMUv7WDA5nnLKG8UrBE3LIKs5KASCe5rsUooS6YgfkKKXbzNc1Vc_JgWCqAcnhkHxcuRF_fv-xQo92dBsslmYXjOYGi3kMvRmdLa5Zvfi88FOIbshBGIqNM3m89cVq8l0Y3NQXK-PH9II864xP-PLhPCZXi7NPp-_L5eX5xel8WdoKGJQdXa9bYRA6aFCqCozkdg2AjQWglivLKKdd3WKrlM2hkLzKMe0620KlxDF5t_PeTeseW4vDGI3Xd9H1Jm51ME4_ngzui74JGw2USgZNFpw8CGL4OmEade-SRe_NgGFKmgvGayoUpxl98w96G6Y45PUyJSVnNZM8U7MdZWNIKWK3_wyj-r4tfd-W3reVH7z-e4U9_rueDDQ74JvzuP2PTs8_XJz9kf8CrNijkw</recordid><startdate>20200127</startdate><enddate>20200127</enddate><creator>Xu, Peng</creator><creator>Zhao, Da</creator><creator>Berger, Florian</creator><creator>Hamad, Aboubakr</creator><creator>Rickmeier, Jens</creator><creator>Petzold, Roland</creator><creator>Kondratiuk, Mykhailo</creator><creator>Bohdan, Kostiantyn</creator><creator>Ritter, Tobias</creator><general>Wiley Subscription Services, Inc</general><general>John Wiley and Sons Inc</general><scope>24P</scope><scope>WIN</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-6957-450X</orcidid></search><sort><creationdate>20200127</creationdate><title>Site‐Selective Late‐Stage Aromatic [18F]Fluorination via Aryl Sulfonium Salts</title><author>Xu, Peng ; Zhao, Da ; Berger, Florian ; Hamad, Aboubakr ; Rickmeier, Jens ; Petzold, Roland ; Kondratiuk, Mykhailo ; Bohdan, Kostiantyn ; Ritter, Tobias</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5717-f0bbd3ae7f79e4657a42cb77e9c770c26c1020f8ded66c9c73425c260ffcd7563</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>18F labeling</topic><topic>Aromatic compounds</topic><topic>Communication</topic><topic>Communications</topic><topic>C−H functionalization</topic><topic>Fluorination</topic><topic>late-stage functionalization</topic><topic>Organic chemistry</topic><topic>radiochemistry</topic><topic>Salts</topic><topic>Sulfonium salts</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xu, Peng</creatorcontrib><creatorcontrib>Zhao, Da</creatorcontrib><creatorcontrib>Berger, Florian</creatorcontrib><creatorcontrib>Hamad, Aboubakr</creatorcontrib><creatorcontrib>Rickmeier, Jens</creatorcontrib><creatorcontrib>Petzold, Roland</creatorcontrib><creatorcontrib>Kondratiuk, Mykhailo</creatorcontrib><creatorcontrib>Bohdan, Kostiantyn</creatorcontrib><creatorcontrib>Ritter, Tobias</creatorcontrib><collection>Wiley Online Library Open Access</collection><collection>Wiley Free Content</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xu, Peng</au><au>Zhao, Da</au><au>Berger, Florian</au><au>Hamad, Aboubakr</au><au>Rickmeier, Jens</au><au>Petzold, Roland</au><au>Kondratiuk, Mykhailo</au><au>Bohdan, Kostiantyn</au><au>Ritter, Tobias</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Site‐Selective Late‐Stage Aromatic [18F]Fluorination via Aryl Sulfonium Salts</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2020-01-27</date><risdate>2020</risdate><volume>59</volume><issue>5</issue><spage>1956</spage><epage>1960</epage><pages>1956-1960</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Site‐selective functionalization of C−H bonds in small complex molecules is a long‐standing challenge in organic chemistry. Herein, we report a broadly applicable and site‐selective aromatic C−H dibenzothiophenylation reaction. The conceptual advantage of this transformation is further demonstrated through the two‐step C−H [18F]fluorination of a series of marketed small‐molecule drugs.
A broadly applicable and site‐selective late‐stage aromatic [18F]fluorination reaction is reported. A collection of three electronically different dibenzothiophenes enables 18F labeling of a series of small complex molecules.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>31697427</pmid><doi>10.1002/anie.201912567</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-6957-450X</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie International Edition, 2020-01, Vol.59 (5), p.1956-1960 |
| issn | 1433-7851 1521-3773 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_7004179 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | 18F labeling Aromatic compounds Communication Communications C−H functionalization Fluorination late-stage functionalization Organic chemistry radiochemistry Salts Sulfonium salts |
| title | Site‐Selective Late‐Stage Aromatic [18F]Fluorination via Aryl Sulfonium Salts |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-24T04%3A11%3A48IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Site%E2%80%90Selective%20Late%E2%80%90Stage%20Aromatic%20%5B18F%5DFluorination%20via%20Aryl%20Sulfonium%20Salts&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Xu,%20Peng&rft.date=2020-01-27&rft.volume=59&rft.issue=5&rft.spage=1956&rft.epage=1960&rft.pages=1956-1960&rft.issn=1433-7851&rft.eissn=1521-3773&rft_id=info:doi/10.1002/anie.201912567&rft_dat=%3Cproquest_pubme%3E2344218142%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2344218142&rft_id=info:pmid/31697427&rfr_iscdi=true |