Ruthenium-catalysed decarboxylative unsymmetric dual ortho -/ meta -C-H bond functionalization of arenecarboxylic acids
Here, we describe a ruthenium-catalysed decarboxylative unsymmetric -C-H azaarylation/ -C-H alkylation a traceless directing group relay strategy. The installation of a 2-pyridyl functionality carboxyl directed -C-H activation is critical to promote decarboxylation and enable -C-H bond alkylation to...
Gespeichert in:
| Veröffentlicht in: | Chemical science (Cambridge) 2023-05, Vol.14 (20), p.5470-5476 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 5476 |
|---|---|
| container_issue | 20 |
| container_start_page | 5470 |
| container_title | Chemical science (Cambridge) |
| container_volume | 14 |
| creator | Li, Xiankai Wang, Xiaofei Zhang, Jing |
| description | Here, we describe a ruthenium-catalysed decarboxylative unsymmetric
-C-H azaarylation/
-C-H alkylation
a traceless directing group relay strategy. The installation of a 2-pyridyl functionality
carboxyl directed
-C-H activation is critical to promote decarboxylation and enable
-C-H bond alkylation to streamline the synthesis of 4-azaaryl-benzo-fused five-membered heterocycles. This protocol is characterized by high regio- and chemoselectivity, broad substrate scopes, and good functional group tolerance under redox-neutral conditions. |
| doi_str_mv | 10.1039/d3sc01226c |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_10208063</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2820023339</sourcerecordid><originalsourceid>FETCH-LOGICAL-c448t-342cca1748623ed0c50ecd52a93bbd7cf26f5a31c4f66447bf12d679719ba3d03</originalsourceid><addsrcrecordid>eNpdkdFqFTEQhoMotrS98QEk4I0Ia5NMdrO5ElmrFQpCq9dhNsl6UnY3NdlUT5_ePbYeqrnJMPPxMcxPyAvO3nIG-tRBtowL0dgn5FAwyaumBv10Xwt2QE5yvmbrA-C1UM_JASgBUjN9SH5elmXj51CmyuKC4zZ7R523mPr4azviEm49LXPeTpNfUrDUFRxpTMsm0uqUrk2kVVed0z7Ojg5ltkuIM47hDncFjQPF5Oe9cDWgDS4fk2cDjtmfPPxH5NvHs6_deXXx5dPn7v1FZaVslwqksBa5km0jwDtma-atqwVq6Hun7CCaoUbgVg5NI6XqBy5co7TiukdwDI7Iu3vvTekn76yfl4SjuUlhwrQ1EYP5dzKHjfkebw1ngrWsgdXw-sGQ4o_i82KmkK0fR5x9LNmIVjAmAECv6Kv_0OtY0nqNHcWVbttW8ZV6c0_ZFHNOfthvw5nZZWo-wFX3J9NuhV8-3n-P_k0QfgNDXJ5i</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2817988871</pqid></control><display><type>article</type><title>Ruthenium-catalysed decarboxylative unsymmetric dual ortho -/ meta -C-H bond functionalization of arenecarboxylic acids</title><source>DOAJ Directory of Open Access Journals</source><source>PubMed Central Open Access</source><source>EZB-FREE-00999 freely available EZB journals</source><source>PubMed Central</source><creator>Li, Xiankai ; Wang, Xiaofei ; Zhang, Jing</creator><creatorcontrib>Li, Xiankai ; Wang, Xiaofei ; Zhang, Jing</creatorcontrib><description>Here, we describe a ruthenium-catalysed decarboxylative unsymmetric
-C-H azaarylation/
-C-H alkylation
a traceless directing group relay strategy. The installation of a 2-pyridyl functionality
carboxyl directed
-C-H activation is critical to promote decarboxylation and enable
-C-H bond alkylation to streamline the synthesis of 4-azaaryl-benzo-fused five-membered heterocycles. This protocol is characterized by high regio- and chemoselectivity, broad substrate scopes, and good functional group tolerance under redox-neutral conditions.</description><identifier>ISSN: 2041-6520</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/d3sc01226c</identifier><identifier>PMID: 37234909</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alkylation ; Chemistry ; Decarboxylation ; Functional groups ; Hydrogen bonds ; Ruthenium ; Substrates</subject><ispartof>Chemical science (Cambridge), 2023-05, Vol.14 (20), p.5470-5476</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2023</rights><rights>This journal is © The Royal Society of Chemistry 2023 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c448t-342cca1748623ed0c50ecd52a93bbd7cf26f5a31c4f66447bf12d679719ba3d03</citedby><cites>FETCH-LOGICAL-c448t-342cca1748623ed0c50ecd52a93bbd7cf26f5a31c4f66447bf12d679719ba3d03</cites><orcidid>0000-0003-3512-8445</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10208063/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10208063/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,315,728,781,785,865,886,27929,27930,53796,53798</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37234909$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Xiankai</creatorcontrib><creatorcontrib>Wang, Xiaofei</creatorcontrib><creatorcontrib>Zhang, Jing</creatorcontrib><title>Ruthenium-catalysed decarboxylative unsymmetric dual ortho -/ meta -C-H bond functionalization of arenecarboxylic acids</title><title>Chemical science (Cambridge)</title><addtitle>Chem Sci</addtitle><description>Here, we describe a ruthenium-catalysed decarboxylative unsymmetric
-C-H azaarylation/
-C-H alkylation
a traceless directing group relay strategy. The installation of a 2-pyridyl functionality
carboxyl directed
-C-H activation is critical to promote decarboxylation and enable
-C-H bond alkylation to streamline the synthesis of 4-azaaryl-benzo-fused five-membered heterocycles. This protocol is characterized by high regio- and chemoselectivity, broad substrate scopes, and good functional group tolerance under redox-neutral conditions.</description><subject>Alkylation</subject><subject>Chemistry</subject><subject>Decarboxylation</subject><subject>Functional groups</subject><subject>Hydrogen bonds</subject><subject>Ruthenium</subject><subject>Substrates</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpdkdFqFTEQhoMotrS98QEk4I0Ia5NMdrO5ElmrFQpCq9dhNsl6UnY3NdlUT5_ePbYeqrnJMPPxMcxPyAvO3nIG-tRBtowL0dgn5FAwyaumBv10Xwt2QE5yvmbrA-C1UM_JASgBUjN9SH5elmXj51CmyuKC4zZ7R523mPr4azviEm49LXPeTpNfUrDUFRxpTMsm0uqUrk2kVVed0z7Ojg5ltkuIM47hDncFjQPF5Oe9cDWgDS4fk2cDjtmfPPxH5NvHs6_deXXx5dPn7v1FZaVslwqksBa5km0jwDtma-atqwVq6Hun7CCaoUbgVg5NI6XqBy5co7TiukdwDI7Iu3vvTekn76yfl4SjuUlhwrQ1EYP5dzKHjfkebw1ngrWsgdXw-sGQ4o_i82KmkK0fR5x9LNmIVjAmAECv6Kv_0OtY0nqNHcWVbttW8ZV6c0_ZFHNOfthvw5nZZWo-wFX3J9NuhV8-3n-P_k0QfgNDXJ5i</recordid><startdate>20230524</startdate><enddate>20230524</enddate><creator>Li, Xiankai</creator><creator>Wang, Xiaofei</creator><creator>Zhang, Jing</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0003-3512-8445</orcidid></search><sort><creationdate>20230524</creationdate><title>Ruthenium-catalysed decarboxylative unsymmetric dual ortho -/ meta -C-H bond functionalization of arenecarboxylic acids</title><author>Li, Xiankai ; Wang, Xiaofei ; Zhang, Jing</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c448t-342cca1748623ed0c50ecd52a93bbd7cf26f5a31c4f66447bf12d679719ba3d03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Alkylation</topic><topic>Chemistry</topic><topic>Decarboxylation</topic><topic>Functional groups</topic><topic>Hydrogen bonds</topic><topic>Ruthenium</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Xiankai</creatorcontrib><creatorcontrib>Wang, Xiaofei</creatorcontrib><creatorcontrib>Zhang, Jing</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Xiankai</au><au>Wang, Xiaofei</au><au>Zhang, Jing</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ruthenium-catalysed decarboxylative unsymmetric dual ortho -/ meta -C-H bond functionalization of arenecarboxylic acids</atitle><jtitle>Chemical science (Cambridge)</jtitle><addtitle>Chem Sci</addtitle><date>2023-05-24</date><risdate>2023</risdate><volume>14</volume><issue>20</issue><spage>5470</spage><epage>5476</epage><pages>5470-5476</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>Here, we describe a ruthenium-catalysed decarboxylative unsymmetric
-C-H azaarylation/
-C-H alkylation
a traceless directing group relay strategy. The installation of a 2-pyridyl functionality
carboxyl directed
-C-H activation is critical to promote decarboxylation and enable
-C-H bond alkylation to streamline the synthesis of 4-azaaryl-benzo-fused five-membered heterocycles. This protocol is characterized by high regio- and chemoselectivity, broad substrate scopes, and good functional group tolerance under redox-neutral conditions.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>37234909</pmid><doi>10.1039/d3sc01226c</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0003-3512-8445</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2041-6520 |
| ispartof | Chemical science (Cambridge), 2023-05, Vol.14 (20), p.5470-5476 |
| issn | 2041-6520 2041-6539 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_10208063 |
| source | DOAJ Directory of Open Access Journals; PubMed Central Open Access; EZB-FREE-00999 freely available EZB journals; PubMed Central |
| subjects | Alkylation Chemistry Decarboxylation Functional groups Hydrogen bonds Ruthenium Substrates |
| title | Ruthenium-catalysed decarboxylative unsymmetric dual ortho -/ meta -C-H bond functionalization of arenecarboxylic acids |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-16T04%3A09%3A28IST&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=Ruthenium-catalysed%20decarboxylative%20unsymmetric%20dual%20ortho%20-/%20meta%20-C-H%20bond%20functionalization%20of%20arenecarboxylic%20acids&rft.jtitle=Chemical%20science%20(Cambridge)&rft.au=Li,%20Xiankai&rft.date=2023-05-24&rft.volume=14&rft.issue=20&rft.spage=5470&rft.epage=5476&rft.pages=5470-5476&rft.issn=2041-6520&rft.eissn=2041-6539&rft_id=info:doi/10.1039/d3sc01226c&rft_dat=%3Cproquest_pubme%3E2820023339%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=2817988871&rft_id=info:pmid/37234909&rfr_iscdi=true |