Construction of C−C Axial Chirality via Asymmetric Carbene Insertion into Arene C−H Bonds
By using diazonaphthoquinones and anilines as key reagents and through a point‐to‐axis chiral transfer strategy, the atroposelective synthesis via asymmetric C(sp2)−H bond insertion reaction of arenes has been realized under rhodium catalysis, providing the resulting biaryl atropisomers in moderate...
Gespeichert in:
| Veröffentlicht in: | Angewandte Chemie International Edition 2021-12, Vol.60 (49), p.25714-25718 |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 25718 |
|---|---|
| container_issue | 49 |
| container_start_page | 25714 |
| container_title | Angewandte Chemie International Edition |
| container_volume | 60 |
| creator | Li, Ziyong Chen, Ying Wang, Chuang Xu, Guangyang Shao, Ying Zhang, Xinhao Tang, Shengbiao Sun, Jiangtao |
| description | By using diazonaphthoquinones and anilines as key reagents and through a point‐to‐axis chiral transfer strategy, the atroposelective synthesis via asymmetric C(sp2)−H bond insertion reaction of arenes has been realized under rhodium catalysis, providing the resulting biaryl atropisomers in moderate to excellent yields with good enantiomeric ratios (up to 99:1). Further elaboration indicates this type of axially biaryl scaffold may have promising potentials in developing novel chiral ligands.
By using diazonaphthoquinones and anilines as key reagents and through a point‐to‐axis chiral transfer strategy, the atroposelective synthesis via asymmetric C(sp2)−H bond insertion reaction of arenes has been realized under rhodium catalysis, providing the resulting biaryl atropisomers in moderate to excellent yields with good enantiomeric ratios (up to 99:1). |
| doi_str_mv | 10.1002/anie.202110430 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2578765671</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2578765671</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3500-5602850c4e2e89e5409c541ea4bd4792815880f19102da1770bcf5462c6a06413</originalsourceid><addsrcrecordid>eNqFkL1OwzAURi0EEqWwMltiYUmxHf8kY4gKrVTBAiOyXNcRrhK72CmQN2DmEXkSEopAYmG6V1fnu_p0ADjFaIIRIhfKWTMhiGCMaIr2wAgzgpNUiHS_32maJiJj-BAcxbju-SxDfAQeSu9iG7a6td5BX8Hy4-29hMWrVTUsH21QtW07-GwVLGLXNKYNVsNShaVxBs5dNOEraV3rYRGG4_BhBi-9W8VjcFCpOpqT7zkG91fTu3KWLG6v52WxSHTKEEoY7-swpKkhJssNoyjXjGKj6HJFRU4yzPq2Fc4xIiuFhUBLXTHKieYKcYrTMTjf_d0E_7Q1sZWNjdrUtXLGb6MkTGSCMy4G9OwPuvbb4Pp2knCEKROsNzYGkx2lg48xmEpugm1U6CRGcrAtB9vyx3YfyHeBF1ub7h9aFjfz6W_2E56wgoU</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2601457577</pqid></control><display><type>article</type><title>Construction of C−C Axial Chirality via Asymmetric Carbene Insertion into Arene C−H Bonds</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Li, Ziyong ; Chen, Ying ; Wang, Chuang ; Xu, Guangyang ; Shao, Ying ; Zhang, Xinhao ; Tang, Shengbiao ; Sun, Jiangtao</creator><creatorcontrib>Li, Ziyong ; Chen, Ying ; Wang, Chuang ; Xu, Guangyang ; Shao, Ying ; Zhang, Xinhao ; Tang, Shengbiao ; Sun, Jiangtao</creatorcontrib><description>By using diazonaphthoquinones and anilines as key reagents and through a point‐to‐axis chiral transfer strategy, the atroposelective synthesis via asymmetric C(sp2)−H bond insertion reaction of arenes has been realized under rhodium catalysis, providing the resulting biaryl atropisomers in moderate to excellent yields with good enantiomeric ratios (up to 99:1). Further elaboration indicates this type of axially biaryl scaffold may have promising potentials in developing novel chiral ligands.
By using diazonaphthoquinones and anilines as key reagents and through a point‐to‐axis chiral transfer strategy, the atroposelective synthesis via asymmetric C(sp2)−H bond insertion reaction of arenes has been realized under rhodium catalysis, providing the resulting biaryl atropisomers in moderate to excellent yields with good enantiomeric ratios (up to 99:1).</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202110430</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Aniline ; Aromatic compounds ; asymmetric catalysis ; Asymmetry ; atropisomer ; axial chirality ; carbene ; Catalysis ; Chirality ; C–H insertion ; Hydrogen bonds ; Insertion ; Reagents ; Rhodium</subject><ispartof>Angewandte Chemie International Edition, 2021-12, Vol.60 (49), p.25714-25718</ispartof><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3500-5602850c4e2e89e5409c541ea4bd4792815880f19102da1770bcf5462c6a06413</citedby><cites>FETCH-LOGICAL-c3500-5602850c4e2e89e5409c541ea4bd4792815880f19102da1770bcf5462c6a06413</cites><orcidid>0000-0003-2516-3466</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.202110430$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202110430$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Li, Ziyong</creatorcontrib><creatorcontrib>Chen, Ying</creatorcontrib><creatorcontrib>Wang, Chuang</creatorcontrib><creatorcontrib>Xu, Guangyang</creatorcontrib><creatorcontrib>Shao, Ying</creatorcontrib><creatorcontrib>Zhang, Xinhao</creatorcontrib><creatorcontrib>Tang, Shengbiao</creatorcontrib><creatorcontrib>Sun, Jiangtao</creatorcontrib><title>Construction of C−C Axial Chirality via Asymmetric Carbene Insertion into Arene C−H Bonds</title><title>Angewandte Chemie International Edition</title><description>By using diazonaphthoquinones and anilines as key reagents and through a point‐to‐axis chiral transfer strategy, the atroposelective synthesis via asymmetric C(sp2)−H bond insertion reaction of arenes has been realized under rhodium catalysis, providing the resulting biaryl atropisomers in moderate to excellent yields with good enantiomeric ratios (up to 99:1). Further elaboration indicates this type of axially biaryl scaffold may have promising potentials in developing novel chiral ligands.
By using diazonaphthoquinones and anilines as key reagents and through a point‐to‐axis chiral transfer strategy, the atroposelective synthesis via asymmetric C(sp2)−H bond insertion reaction of arenes has been realized under rhodium catalysis, providing the resulting biaryl atropisomers in moderate to excellent yields with good enantiomeric ratios (up to 99:1).</description><subject>Aniline</subject><subject>Aromatic compounds</subject><subject>asymmetric catalysis</subject><subject>Asymmetry</subject><subject>atropisomer</subject><subject>axial chirality</subject><subject>carbene</subject><subject>Catalysis</subject><subject>Chirality</subject><subject>C–H insertion</subject><subject>Hydrogen bonds</subject><subject>Insertion</subject><subject>Reagents</subject><subject>Rhodium</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkL1OwzAURi0EEqWwMltiYUmxHf8kY4gKrVTBAiOyXNcRrhK72CmQN2DmEXkSEopAYmG6V1fnu_p0ADjFaIIRIhfKWTMhiGCMaIr2wAgzgpNUiHS_32maJiJj-BAcxbju-SxDfAQeSu9iG7a6td5BX8Hy4-29hMWrVTUsH21QtW07-GwVLGLXNKYNVsNShaVxBs5dNOEraV3rYRGG4_BhBi-9W8VjcFCpOpqT7zkG91fTu3KWLG6v52WxSHTKEEoY7-swpKkhJssNoyjXjGKj6HJFRU4yzPq2Fc4xIiuFhUBLXTHKieYKcYrTMTjf_d0E_7Q1sZWNjdrUtXLGb6MkTGSCMy4G9OwPuvbb4Pp2knCEKROsNzYGkx2lg48xmEpugm1U6CRGcrAtB9vyx3YfyHeBF1ub7h9aFjfz6W_2E56wgoU</recordid><startdate>20211201</startdate><enddate>20211201</enddate><creator>Li, Ziyong</creator><creator>Chen, Ying</creator><creator>Wang, Chuang</creator><creator>Xu, Guangyang</creator><creator>Shao, Ying</creator><creator>Zhang, Xinhao</creator><creator>Tang, Shengbiao</creator><creator>Sun, Jiangtao</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-2516-3466</orcidid></search><sort><creationdate>20211201</creationdate><title>Construction of C−C Axial Chirality via Asymmetric Carbene Insertion into Arene C−H Bonds</title><author>Li, Ziyong ; Chen, Ying ; Wang, Chuang ; Xu, Guangyang ; Shao, Ying ; Zhang, Xinhao ; Tang, Shengbiao ; Sun, Jiangtao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3500-5602850c4e2e89e5409c541ea4bd4792815880f19102da1770bcf5462c6a06413</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Aniline</topic><topic>Aromatic compounds</topic><topic>asymmetric catalysis</topic><topic>Asymmetry</topic><topic>atropisomer</topic><topic>axial chirality</topic><topic>carbene</topic><topic>Catalysis</topic><topic>Chirality</topic><topic>C–H insertion</topic><topic>Hydrogen bonds</topic><topic>Insertion</topic><topic>Reagents</topic><topic>Rhodium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Ziyong</creatorcontrib><creatorcontrib>Chen, Ying</creatorcontrib><creatorcontrib>Wang, Chuang</creatorcontrib><creatorcontrib>Xu, Guangyang</creatorcontrib><creatorcontrib>Shao, Ying</creatorcontrib><creatorcontrib>Zhang, Xinhao</creatorcontrib><creatorcontrib>Tang, Shengbiao</creatorcontrib><creatorcontrib>Sun, Jiangtao</creatorcontrib><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Ziyong</au><au>Chen, Ying</au><au>Wang, Chuang</au><au>Xu, Guangyang</au><au>Shao, Ying</au><au>Zhang, Xinhao</au><au>Tang, Shengbiao</au><au>Sun, Jiangtao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Construction of C−C Axial Chirality via Asymmetric Carbene Insertion into Arene C−H Bonds</atitle><jtitle>Angewandte Chemie International Edition</jtitle><date>2021-12-01</date><risdate>2021</risdate><volume>60</volume><issue>49</issue><spage>25714</spage><epage>25718</epage><pages>25714-25718</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>By using diazonaphthoquinones and anilines as key reagents and through a point‐to‐axis chiral transfer strategy, the atroposelective synthesis via asymmetric C(sp2)−H bond insertion reaction of arenes has been realized under rhodium catalysis, providing the resulting biaryl atropisomers in moderate to excellent yields with good enantiomeric ratios (up to 99:1). Further elaboration indicates this type of axially biaryl scaffold may have promising potentials in developing novel chiral ligands.
By using diazonaphthoquinones and anilines as key reagents and through a point‐to‐axis chiral transfer strategy, the atroposelective synthesis via asymmetric C(sp2)−H bond insertion reaction of arenes has been realized under rhodium catalysis, providing the resulting biaryl atropisomers in moderate to excellent yields with good enantiomeric ratios (up to 99:1).</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/anie.202110430</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0003-2516-3466</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie International Edition, 2021-12, Vol.60 (49), p.25714-25718 |
| issn | 1433-7851 1521-3773 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2578765671 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Aniline Aromatic compounds asymmetric catalysis Asymmetry atropisomer axial chirality carbene Catalysis Chirality C–H insertion Hydrogen bonds Insertion Reagents Rhodium |
| title | Construction of C−C Axial Chirality via Asymmetric Carbene Insertion into Arene C−H Bonds |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-02T09%3A01%3A55IST&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=Construction%20of%20C%E2%88%92C%20Axial%20Chirality%20via%20Asymmetric%20Carbene%20Insertion%20into%20Arene%20C%E2%88%92H%20Bonds&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Li,%20Ziyong&rft.date=2021-12-01&rft.volume=60&rft.issue=49&rft.spage=25714&rft.epage=25718&rft.pages=25714-25718&rft.issn=1433-7851&rft.eissn=1521-3773&rft_id=info:doi/10.1002/anie.202110430&rft_dat=%3Cproquest_cross%3E2578765671%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=2601457577&rft_id=info:pmid/&rfr_iscdi=true |