Iterative C−H Functionalization Leading to Multiple Amidations of Anilides
Polyaminobenzenes were synthesized by the ruthenium‐catalyzed iterative C−H amidation of anilides using dioxazolones as an amino source. This strategy could be implemented by the sequential activation of C−H bonds of formerly generated compounds by cascade chelation assistance of newly installed ami...
Gespeichert in:
| Veröffentlicht in: | Angewandte Chemie International Edition 2017-04, Vol.56 (15), p.4256-4260 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 4260 |
|---|---|
| container_issue | 15 |
| container_start_page | 4256 |
| container_title | Angewandte Chemie International Edition |
| container_volume | 56 |
| creator | Park, Juhyeon Lee, Jia Chang, Sukbok |
| description | Polyaminobenzenes were synthesized by the ruthenium‐catalyzed iterative C−H amidation of anilides using dioxazolones as an amino source. This strategy could be implemented by the sequential activation of C−H bonds of formerly generated compounds by cascade chelation assistance of newly installed amide groups. Computational studies provided a rationale.
Repeat performance: A ruthenium‐catalyzed cascade amidation of multiple C−H bonds of anilide has been developed. By using dioxazolone as amidating reagents, newly installed amide groups serve as an additional directing groups to drive subsequent C−H activation. This reaction provides a simple and mild approach to the preparation of polyaminobenzenes. |
| doi_str_mv | 10.1002/anie.201701138 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1877852547</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1877852547</sourcerecordid><originalsourceid>FETCH-LOGICAL-c5048-6b60c57ffb744adead0173ec8cbba01a285d8c913a288075a701831eb62137453</originalsourceid><addsrcrecordid>eNqFkb1OwzAUhS0EoqWwMqJILCwp_o2dMapaWinAArPlJA5ylZ8SJ6DyBMw8Ik-C05YiMcB0r3S_e3TPPQCcIzhGEOJrVRk9xhBxiBARB2CIGEY-4Zwcup4S4nPB0ACcWLt0vBAwOAYDLHBIqQiHIF60ulGtedHe5PP9Y-7NuiptTV2pwrypvvFirTJTPXlt7d12RWtWhfai0mSbqfXq3IsqU5hM21NwlKvC6rNdHYHH2fRhMvfj-5vFJIr9lEEq_CAJYMp4niecUpU5eXc_0alIk0RBpLBgmUhDRFR_L2fKmRME6STAiHDKyAhcbXVXTf3cadvK0thUF4WqdN1ZiQR3rjGj3KGXv9Bl3TXOnaNCSCEO3PP-pIRAFAq4ocZbKm1qaxudy1VjStWsJYKyT0P2ach9Gm7hYifbJaXO9vj3-x0QboFXU-j1P3IyultMf8S_AHVMlLE</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1881408001</pqid></control><display><type>article</type><title>Iterative C−H Functionalization Leading to Multiple Amidations of Anilides</title><source>Access via Wiley Online Library</source><creator>Park, Juhyeon ; Lee, Jia ; Chang, Sukbok</creator><creatorcontrib>Park, Juhyeon ; Lee, Jia ; Chang, Sukbok</creatorcontrib><description>Polyaminobenzenes were synthesized by the ruthenium‐catalyzed iterative C−H amidation of anilides using dioxazolones as an amino source. This strategy could be implemented by the sequential activation of C−H bonds of formerly generated compounds by cascade chelation assistance of newly installed amide groups. Computational studies provided a rationale.
Repeat performance: A ruthenium‐catalyzed cascade amidation of multiple C−H bonds of anilide has been developed. By using dioxazolone as amidating reagents, newly installed amide groups serve as an additional directing groups to drive subsequent C−H activation. This reaction provides a simple and mild approach to the preparation of polyaminobenzenes.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201701138</identifier><identifier>PMID: 28294489</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>amidation ; arenes ; Chelation ; Chemical bonds ; Chemical synthesis ; Computer applications ; C−H activation ; reaction mechanisms ; Ruthenium</subject><ispartof>Angewandte Chemie International Edition, 2017-04, Vol.56 (15), p.4256-4260</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5048-6b60c57ffb744adead0173ec8cbba01a285d8c913a288075a701831eb62137453</citedby><cites>FETCH-LOGICAL-c5048-6b60c57ffb744adead0173ec8cbba01a285d8c913a288075a701831eb62137453</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.201701138$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201701138$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28294489$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Park, Juhyeon</creatorcontrib><creatorcontrib>Lee, Jia</creatorcontrib><creatorcontrib>Chang, Sukbok</creatorcontrib><title>Iterative C−H Functionalization Leading to Multiple Amidations of Anilides</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>Polyaminobenzenes were synthesized by the ruthenium‐catalyzed iterative C−H amidation of anilides using dioxazolones as an amino source. This strategy could be implemented by the sequential activation of C−H bonds of formerly generated compounds by cascade chelation assistance of newly installed amide groups. Computational studies provided a rationale.
Repeat performance: A ruthenium‐catalyzed cascade amidation of multiple C−H bonds of anilide has been developed. By using dioxazolone as amidating reagents, newly installed amide groups serve as an additional directing groups to drive subsequent C−H activation. This reaction provides a simple and mild approach to the preparation of polyaminobenzenes.</description><subject>amidation</subject><subject>arenes</subject><subject>Chelation</subject><subject>Chemical bonds</subject><subject>Chemical synthesis</subject><subject>Computer applications</subject><subject>C−H activation</subject><subject>reaction mechanisms</subject><subject>Ruthenium</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkb1OwzAUhS0EoqWwMqJILCwp_o2dMapaWinAArPlJA5ylZ8SJ6DyBMw8Ik-C05YiMcB0r3S_e3TPPQCcIzhGEOJrVRk9xhBxiBARB2CIGEY-4Zwcup4S4nPB0ACcWLt0vBAwOAYDLHBIqQiHIF60ulGtedHe5PP9Y-7NuiptTV2pwrypvvFirTJTPXlt7d12RWtWhfai0mSbqfXq3IsqU5hM21NwlKvC6rNdHYHH2fRhMvfj-5vFJIr9lEEq_CAJYMp4niecUpU5eXc_0alIk0RBpLBgmUhDRFR_L2fKmRME6STAiHDKyAhcbXVXTf3cadvK0thUF4WqdN1ZiQR3rjGj3KGXv9Bl3TXOnaNCSCEO3PP-pIRAFAq4ocZbKm1qaxudy1VjStWsJYKyT0P2ach9Gm7hYifbJaXO9vj3-x0QboFXU-j1P3IyultMf8S_AHVMlLE</recordid><startdate>20170403</startdate><enddate>20170403</enddate><creator>Park, Juhyeon</creator><creator>Lee, Jia</creator><creator>Chang, Sukbok</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20170403</creationdate><title>Iterative C−H Functionalization Leading to Multiple Amidations of Anilides</title><author>Park, Juhyeon ; Lee, Jia ; Chang, Sukbok</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5048-6b60c57ffb744adead0173ec8cbba01a285d8c913a288075a701831eb62137453</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>amidation</topic><topic>arenes</topic><topic>Chelation</topic><topic>Chemical bonds</topic><topic>Chemical synthesis</topic><topic>Computer applications</topic><topic>C−H activation</topic><topic>reaction mechanisms</topic><topic>Ruthenium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Park, Juhyeon</creatorcontrib><creatorcontrib>Lee, Jia</creatorcontrib><creatorcontrib>Chang, Sukbok</creatorcontrib><collection>PubMed</collection><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>Park, Juhyeon</au><au>Lee, Jia</au><au>Chang, Sukbok</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Iterative C−H Functionalization Leading to Multiple Amidations of Anilides</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2017-04-03</date><risdate>2017</risdate><volume>56</volume><issue>15</issue><spage>4256</spage><epage>4260</epage><pages>4256-4260</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>Polyaminobenzenes were synthesized by the ruthenium‐catalyzed iterative C−H amidation of anilides using dioxazolones as an amino source. This strategy could be implemented by the sequential activation of C−H bonds of formerly generated compounds by cascade chelation assistance of newly installed amide groups. Computational studies provided a rationale.
Repeat performance: A ruthenium‐catalyzed cascade amidation of multiple C−H bonds of anilide has been developed. By using dioxazolone as amidating reagents, newly installed amide groups serve as an additional directing groups to drive subsequent C−H activation. This reaction provides a simple and mild approach to the preparation of polyaminobenzenes.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>28294489</pmid><doi>10.1002/anie.201701138</doi><tpages>5</tpages><edition>International ed. in English</edition></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie International Edition, 2017-04, Vol.56 (15), p.4256-4260 |
| issn | 1433-7851 1521-3773 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1877852547 |
| source | Access via Wiley Online Library |
| subjects | amidation arenes Chelation Chemical bonds Chemical synthesis Computer applications C−H activation reaction mechanisms Ruthenium |
| title | Iterative C−H Functionalization Leading to Multiple Amidations of Anilides |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-18T18%3A45%3A51IST&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=Iterative%20C%E2%88%92H%20Functionalization%20Leading%20to%20Multiple%20Amidations%20of%20Anilides&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Park,%20Juhyeon&rft.date=2017-04-03&rft.volume=56&rft.issue=15&rft.spage=4256&rft.epage=4260&rft.pages=4256-4260&rft.issn=1433-7851&rft.eissn=1521-3773&rft.coden=ACIEAY&rft_id=info:doi/10.1002/anie.201701138&rft_dat=%3Cproquest_cross%3E1877852547%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=1881408001&rft_id=info:pmid/28294489&rfr_iscdi=true |