N-Heterocyclic-Carbene-Catalyzed Synthesis of 2-Aryl Indoles
A convergent and efficient transition‐metal‐free catalytic synthesis of 2‐aryl‐indoles has been developed. The interception of a highly reactive and transient aza‐ortho‐quinone methide by an acyl anion equivalent generated through N‐hetereocyclic carbene catalysis is central to this successful strat...
Gespeichert in:
| Veröffentlicht in: | Angewandte Chemie International Edition 2014-09, Vol.53 (36), p.9603-9607 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 9607 |
|---|---|
| container_issue | 36 |
| container_start_page | 9603 |
| container_title | Angewandte Chemie International Edition |
| container_volume | 53 |
| creator | Hovey, M. Todd Check, Christopher T. Sipher, Alexandra F. Scheidt, Karl A. |
| description | A convergent and efficient transition‐metal‐free catalytic synthesis of 2‐aryl‐indoles has been developed. The interception of a highly reactive and transient aza‐ortho‐quinone methide by an acyl anion equivalent generated through N‐hetereocyclic carbene catalysis is central to this successful strategy. High yields and a wide scope as well as the streamlined synthesis of a kinase inhibitor are reported.
Umpolung: N‐heterocyclic carbene catalysis is used for the convergent and efficient transition‐metal‐free synthesis of 2‐aryl‐indoles. The interception of a highly reactive and transient aza‐ortho‐quinone methide by an acyl anion equivalent is central to this successful strategy. The reaction exhibits high yields and a wide scope, and it has been applied to a streamlined synthesis of a kinase inhibitor. |
| doi_str_mv | 10.1002/anie.201405035 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_4164393</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1558526321</sourcerecordid><originalsourceid>FETCH-LOGICAL-c6465-3fc46aae5ccd5e10280d81ce9fca8e66a09ad4c595900097e380bf1bdb48883a3</originalsourceid><addsrcrecordid>eNqFkc1vEzEQxS0EoqXlyhFF4sLFwV5_rC0hpCgqbaQSWijiaHm9s9TFWbf2hnb563GUEhUuPc1I83tPM_MQekXJlBJSvbO9h2lFKCeCMPEE7VNRUczqmj0tPWcM10rQPfQi56vCK0Xkc7RXCcK5omIfvV_iExggRTe64B2e29RAD6UONoy_oZ18HfvhErLPk9hNKjxLY5gs-jYGyIfoWWdDhpf39QB9-3h0MT_Bp5-PF_PZKXaSS4FZ57i0FoRzrQBatiCtog5056wCKS3RtuVOaKEJIboGpkjT0aZtuFKKWXaAPmx9r9fNCloH_ZBsMNfJr2waTbTe_Dvp_aX5EX8ZTiVnmhWDt_cGKd6sIQ9m5bODEGwPcZ0NrQklmgpWPY4KoUQlWUUL-uY_9CquU18-saFqysotulDTLeVSzDlBt9ubErPJ0GwyNLsMi-D1w2t3-N_QCqC3wK0PMD5iZ2bLxdFDc7zV-jzA3U5r008ja1YL8315bPT87MvFJ31uztkfcH-2oA</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1557130979</pqid></control><display><type>article</type><title>N-Heterocyclic-Carbene-Catalyzed Synthesis of 2-Aryl Indoles</title><source>MEDLINE</source><source>Wiley Online Library Journals Frontfile Complete</source><creator>Hovey, M. Todd ; Check, Christopher T. ; Sipher, Alexandra F. ; Scheidt, Karl A.</creator><creatorcontrib>Hovey, M. Todd ; Check, Christopher T. ; Sipher, Alexandra F. ; Scheidt, Karl A.</creatorcontrib><description>A convergent and efficient transition‐metal‐free catalytic synthesis of 2‐aryl‐indoles has been developed. The interception of a highly reactive and transient aza‐ortho‐quinone methide by an acyl anion equivalent generated through N‐hetereocyclic carbene catalysis is central to this successful strategy. High yields and a wide scope as well as the streamlined synthesis of a kinase inhibitor are reported.
Umpolung: N‐heterocyclic carbene catalysis is used for the convergent and efficient transition‐metal‐free synthesis of 2‐aryl‐indoles. The interception of a highly reactive and transient aza‐ortho‐quinone methide by an acyl anion equivalent is central to this successful strategy. The reaction exhibits high yields and a wide scope, and it has been applied to a streamlined synthesis of a kinase inhibitor.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201405035</identifier><identifier>PMID: 25044815</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Anions ; asymmetric synthesis ; Aza Compounds - chemistry ; Carbenes ; Catalysis ; cooperative effects ; Equivalence ; Heterocyclic Compounds - chemical synthesis ; Indoles - chemical synthesis ; Inhibitors ; Interception ; Kinases ; Methane - analogs & derivatives ; Methane - chemistry ; Protein Kinase Inhibitors - chemical synthesis ; Stereoisomerism ; Strategy ; Synthesis</subject><ispartof>Angewandte Chemie International Edition, 2014-09, Vol.53 (36), p.9603-9607</ispartof><rights>2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6465-3fc46aae5ccd5e10280d81ce9fca8e66a09ad4c595900097e380bf1bdb48883a3</citedby><cites>FETCH-LOGICAL-c6465-3fc46aae5ccd5e10280d81ce9fca8e66a09ad4c595900097e380bf1bdb48883a3</cites></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.201405035$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201405035$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,314,778,782,883,1414,27907,27908,45557,45558</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25044815$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hovey, M. Todd</creatorcontrib><creatorcontrib>Check, Christopher T.</creatorcontrib><creatorcontrib>Sipher, Alexandra F.</creatorcontrib><creatorcontrib>Scheidt, Karl A.</creatorcontrib><title>N-Heterocyclic-Carbene-Catalyzed Synthesis of 2-Aryl Indoles</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>A convergent and efficient transition‐metal‐free catalytic synthesis of 2‐aryl‐indoles has been developed. The interception of a highly reactive and transient aza‐ortho‐quinone methide by an acyl anion equivalent generated through N‐hetereocyclic carbene catalysis is central to this successful strategy. High yields and a wide scope as well as the streamlined synthesis of a kinase inhibitor are reported.
Umpolung: N‐heterocyclic carbene catalysis is used for the convergent and efficient transition‐metal‐free synthesis of 2‐aryl‐indoles. The interception of a highly reactive and transient aza‐ortho‐quinone methide by an acyl anion equivalent is central to this successful strategy. The reaction exhibits high yields and a wide scope, and it has been applied to a streamlined synthesis of a kinase inhibitor.</description><subject>Anions</subject><subject>asymmetric synthesis</subject><subject>Aza Compounds - chemistry</subject><subject>Carbenes</subject><subject>Catalysis</subject><subject>cooperative effects</subject><subject>Equivalence</subject><subject>Heterocyclic Compounds - chemical synthesis</subject><subject>Indoles - chemical synthesis</subject><subject>Inhibitors</subject><subject>Interception</subject><subject>Kinases</subject><subject>Methane - analogs & derivatives</subject><subject>Methane - chemistry</subject><subject>Protein Kinase Inhibitors - chemical synthesis</subject><subject>Stereoisomerism</subject><subject>Strategy</subject><subject>Synthesis</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc1vEzEQxS0EoqXlyhFF4sLFwV5_rC0hpCgqbaQSWijiaHm9s9TFWbf2hnb563GUEhUuPc1I83tPM_MQekXJlBJSvbO9h2lFKCeCMPEE7VNRUczqmj0tPWcM10rQPfQi56vCK0Xkc7RXCcK5omIfvV_iExggRTe64B2e29RAD6UONoy_oZ18HfvhErLPk9hNKjxLY5gs-jYGyIfoWWdDhpf39QB9-3h0MT_Bp5-PF_PZKXaSS4FZ57i0FoRzrQBatiCtog5056wCKS3RtuVOaKEJIboGpkjT0aZtuFKKWXaAPmx9r9fNCloH_ZBsMNfJr2waTbTe_Dvp_aX5EX8ZTiVnmhWDt_cGKd6sIQ9m5bODEGwPcZ0NrQklmgpWPY4KoUQlWUUL-uY_9CquU18-saFqysotulDTLeVSzDlBt9ubErPJ0GwyNLsMi-D1w2t3-N_QCqC3wK0PMD5iZ2bLxdFDc7zV-jzA3U5r008ja1YL8315bPT87MvFJ31uztkfcH-2oA</recordid><startdate>20140901</startdate><enddate>20140901</enddate><creator>Hovey, M. Todd</creator><creator>Check, Christopher T.</creator><creator>Sipher, Alexandra F.</creator><creator>Scheidt, Karl A.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><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>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>5PM</scope></search><sort><creationdate>20140901</creationdate><title>N-Heterocyclic-Carbene-Catalyzed Synthesis of 2-Aryl Indoles</title><author>Hovey, M. Todd ; Check, Christopher T. ; Sipher, Alexandra F. ; Scheidt, Karl A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6465-3fc46aae5ccd5e10280d81ce9fca8e66a09ad4c595900097e380bf1bdb48883a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Anions</topic><topic>asymmetric synthesis</topic><topic>Aza Compounds - chemistry</topic><topic>Carbenes</topic><topic>Catalysis</topic><topic>cooperative effects</topic><topic>Equivalence</topic><topic>Heterocyclic Compounds - chemical synthesis</topic><topic>Indoles - chemical synthesis</topic><topic>Inhibitors</topic><topic>Interception</topic><topic>Kinases</topic><topic>Methane - analogs & derivatives</topic><topic>Methane - chemistry</topic><topic>Protein Kinase Inhibitors - chemical synthesis</topic><topic>Stereoisomerism</topic><topic>Strategy</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hovey, M. Todd</creatorcontrib><creatorcontrib>Check, Christopher T.</creatorcontrib><creatorcontrib>Sipher, Alexandra F.</creatorcontrib><creatorcontrib>Scheidt, Karl A.</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</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>Hovey, M. Todd</au><au>Check, Christopher T.</au><au>Sipher, Alexandra F.</au><au>Scheidt, Karl A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>N-Heterocyclic-Carbene-Catalyzed Synthesis of 2-Aryl Indoles</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2014-09-01</date><risdate>2014</risdate><volume>53</volume><issue>36</issue><spage>9603</spage><epage>9607</epage><pages>9603-9607</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>A convergent and efficient transition‐metal‐free catalytic synthesis of 2‐aryl‐indoles has been developed. The interception of a highly reactive and transient aza‐ortho‐quinone methide by an acyl anion equivalent generated through N‐hetereocyclic carbene catalysis is central to this successful strategy. High yields and a wide scope as well as the streamlined synthesis of a kinase inhibitor are reported.
Umpolung: N‐heterocyclic carbene catalysis is used for the convergent and efficient transition‐metal‐free synthesis of 2‐aryl‐indoles. The interception of a highly reactive and transient aza‐ortho‐quinone methide by an acyl anion equivalent is central to this successful strategy. The reaction exhibits high yields and a wide scope, and it has been applied to a streamlined synthesis of a kinase inhibitor.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25044815</pmid><doi>10.1002/anie.201405035</doi><tpages>5</tpages><edition>International ed. in English</edition><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie International Edition, 2014-09, Vol.53 (36), p.9603-9607 |
| issn | 1433-7851 1521-3773 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_4164393 |
| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Anions asymmetric synthesis Aza Compounds - chemistry Carbenes Catalysis cooperative effects Equivalence Heterocyclic Compounds - chemical synthesis Indoles - chemical synthesis Inhibitors Interception Kinases Methane - analogs & derivatives Methane - chemistry Protein Kinase Inhibitors - chemical synthesis Stereoisomerism Strategy Synthesis |
| title | N-Heterocyclic-Carbene-Catalyzed Synthesis of 2-Aryl Indoles |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-16T21%3A50%3A22IST&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=N-Heterocyclic-Carbene-Catalyzed%20Synthesis%20of%202-Aryl%20Indoles&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Hovey,%20M.%20Todd&rft.date=2014-09-01&rft.volume=53&rft.issue=36&rft.spage=9603&rft.epage=9607&rft.pages=9603-9607&rft.issn=1433-7851&rft.eissn=1521-3773&rft.coden=ACIEAY&rft_id=info:doi/10.1002/anie.201405035&rft_dat=%3Cproquest_pubme%3E1558526321%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=1557130979&rft_id=info:pmid/25044815&rfr_iscdi=true |