Directed Cobalt-Catalyzed anti -Markovnikov Hydroalkylation of Unactivated Alkenes Enabled by "Co-H" Catalysis
The earth-abundant cobalt-catalyzed -Markovnikov hydroalkylation of unactivated alkenes with oxime esters was achieved by introducing an 8-aminoquinoline directing group on the alkenes. The catalytic system, consisting of commercially available Co(acac) and PhMeSiH , enables the construction of unfu...
Gespeichert in:
| Veröffentlicht in: | Organic letters 2020-06, Vol.22 (11), p.4333-4338 |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 4338 |
|---|---|
| container_issue | 11 |
| container_start_page | 4333 |
| container_title | Organic letters |
| container_volume | 22 |
| creator | Yang, Dandan Huang, Hai Li, Meng-Hui Si, Xiao-Ju Zhang, He Niu, Jun-Long Song, Mao-Ping |
| description | The earth-abundant cobalt-catalyzed
-Markovnikov hydroalkylation of unactivated alkenes with oxime esters was achieved by introducing an 8-aminoquinoline directing group on the alkenes. The catalytic system, consisting of commercially available Co(acac)
and PhMeSiH
, enables the construction of unfunctionalized C(sp
)-C(sp
) bonds and features exclusive
-Markovnikov selectivity, good functional group tolerance, and the avoidance of an extra ligand, oxidant, or base. Mechanistic insight into this new catalytic system indicates the involvement of both alkyl radical and cobalt hydride intermediates. |
| doi_str_mv | 10.1021/acs.orglett.0c01365 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2403030293</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2403030293</sourcerecordid><originalsourceid>FETCH-LOGICAL-c305t-795817fede8ed8fe6147128ce161f12d286e13309410811c94c25b01265ecd683</originalsourceid><addsrcrecordid>eNo9kN9LwzAQx4Mobk7_AkHKnnzpzCX9-TjqdMLEF_dc0vQqdVkzk2xQ_3ozVsfB_eLue9yHkHugM6AMnoS0M22-FDo3o5ICT-ILMoaY8TClMbs85wkdkRtrvykF38mvyYiziELM-Zh0z61B6bAOCl0J5cJCOKH6X98QnWuD8F2YjT50rXfBsq-NFmrTK-Fa3QW6CdadkK49iKPCXG2wQxssOlEpX1d9MC10uJwGJ1Hb2lty1Qhl8W6IE7J-WXwWy3D18fpWzFeh5DR2YZrHGaQN1phhnTWYQJQCyyRCAg2wmmUJAuc0j4BmADKPJIsrCiyJUdZJxifk8aS7M_pnj9aV29ZKVEp0qPe29P9zbyznfpSfRqXR1hpsyp1pt8L0JdDyCLr0oMsBdDmA9lsPw4F9tcX6vPNPlv8By5N8Hg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2403030293</pqid></control><display><type>article</type><title>Directed Cobalt-Catalyzed anti -Markovnikov Hydroalkylation of Unactivated Alkenes Enabled by "Co-H" Catalysis</title><source>ACS Publications</source><creator>Yang, Dandan ; Huang, Hai ; Li, Meng-Hui ; Si, Xiao-Ju ; Zhang, He ; Niu, Jun-Long ; Song, Mao-Ping</creator><creatorcontrib>Yang, Dandan ; Huang, Hai ; Li, Meng-Hui ; Si, Xiao-Ju ; Zhang, He ; Niu, Jun-Long ; Song, Mao-Ping</creatorcontrib><description>The earth-abundant cobalt-catalyzed
-Markovnikov hydroalkylation of unactivated alkenes with oxime esters was achieved by introducing an 8-aminoquinoline directing group on the alkenes. The catalytic system, consisting of commercially available Co(acac)
and PhMeSiH
, enables the construction of unfunctionalized C(sp
)-C(sp
) bonds and features exclusive
-Markovnikov selectivity, good functional group tolerance, and the avoidance of an extra ligand, oxidant, or base. Mechanistic insight into this new catalytic system indicates the involvement of both alkyl radical and cobalt hydride intermediates.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.0c01365</identifier><identifier>PMID: 32401533</identifier><language>eng</language><publisher>United States</publisher><ispartof>Organic letters, 2020-06, Vol.22 (11), p.4333-4338</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c305t-795817fede8ed8fe6147128ce161f12d286e13309410811c94c25b01265ecd683</citedby><cites>FETCH-LOGICAL-c305t-795817fede8ed8fe6147128ce161f12d286e13309410811c94c25b01265ecd683</cites><orcidid>0000-0003-3883-2622 ; 0000-0002-1880-8417 ; 0000-0001-8012-4676</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,2752,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32401533$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yang, Dandan</creatorcontrib><creatorcontrib>Huang, Hai</creatorcontrib><creatorcontrib>Li, Meng-Hui</creatorcontrib><creatorcontrib>Si, Xiao-Ju</creatorcontrib><creatorcontrib>Zhang, He</creatorcontrib><creatorcontrib>Niu, Jun-Long</creatorcontrib><creatorcontrib>Song, Mao-Ping</creatorcontrib><title>Directed Cobalt-Catalyzed anti -Markovnikov Hydroalkylation of Unactivated Alkenes Enabled by "Co-H" Catalysis</title><title>Organic letters</title><addtitle>Org Lett</addtitle><description>The earth-abundant cobalt-catalyzed
-Markovnikov hydroalkylation of unactivated alkenes with oxime esters was achieved by introducing an 8-aminoquinoline directing group on the alkenes. The catalytic system, consisting of commercially available Co(acac)
and PhMeSiH
, enables the construction of unfunctionalized C(sp
)-C(sp
) bonds and features exclusive
-Markovnikov selectivity, good functional group tolerance, and the avoidance of an extra ligand, oxidant, or base. Mechanistic insight into this new catalytic system indicates the involvement of both alkyl radical and cobalt hydride intermediates.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNo9kN9LwzAQx4Mobk7_AkHKnnzpzCX9-TjqdMLEF_dc0vQqdVkzk2xQ_3ozVsfB_eLue9yHkHugM6AMnoS0M22-FDo3o5ICT-ILMoaY8TClMbs85wkdkRtrvykF38mvyYiziELM-Zh0z61B6bAOCl0J5cJCOKH6X98QnWuD8F2YjT50rXfBsq-NFmrTK-Fa3QW6CdadkK49iKPCXG2wQxssOlEpX1d9MC10uJwGJ1Hb2lty1Qhl8W6IE7J-WXwWy3D18fpWzFeh5DR2YZrHGaQN1phhnTWYQJQCyyRCAg2wmmUJAuc0j4BmADKPJIsrCiyJUdZJxifk8aS7M_pnj9aV29ZKVEp0qPe29P9zbyznfpSfRqXR1hpsyp1pt8L0JdDyCLr0oMsBdDmA9lsPw4F9tcX6vPNPlv8By5N8Hg</recordid><startdate>20200605</startdate><enddate>20200605</enddate><creator>Yang, Dandan</creator><creator>Huang, Hai</creator><creator>Li, Meng-Hui</creator><creator>Si, Xiao-Ju</creator><creator>Zhang, He</creator><creator>Niu, Jun-Long</creator><creator>Song, Mao-Ping</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-3883-2622</orcidid><orcidid>https://orcid.org/0000-0002-1880-8417</orcidid><orcidid>https://orcid.org/0000-0001-8012-4676</orcidid></search><sort><creationdate>20200605</creationdate><title>Directed Cobalt-Catalyzed anti -Markovnikov Hydroalkylation of Unactivated Alkenes Enabled by "Co-H" Catalysis</title><author>Yang, Dandan ; Huang, Hai ; Li, Meng-Hui ; Si, Xiao-Ju ; Zhang, He ; Niu, Jun-Long ; Song, Mao-Ping</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c305t-795817fede8ed8fe6147128ce161f12d286e13309410811c94c25b01265ecd683</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yang, Dandan</creatorcontrib><creatorcontrib>Huang, Hai</creatorcontrib><creatorcontrib>Li, Meng-Hui</creatorcontrib><creatorcontrib>Si, Xiao-Ju</creatorcontrib><creatorcontrib>Zhang, He</creatorcontrib><creatorcontrib>Niu, Jun-Long</creatorcontrib><creatorcontrib>Song, Mao-Ping</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yang, Dandan</au><au>Huang, Hai</au><au>Li, Meng-Hui</au><au>Si, Xiao-Ju</au><au>Zhang, He</au><au>Niu, Jun-Long</au><au>Song, Mao-Ping</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Directed Cobalt-Catalyzed anti -Markovnikov Hydroalkylation of Unactivated Alkenes Enabled by "Co-H" Catalysis</atitle><jtitle>Organic letters</jtitle><addtitle>Org Lett</addtitle><date>2020-06-05</date><risdate>2020</risdate><volume>22</volume><issue>11</issue><spage>4333</spage><epage>4338</epage><pages>4333-4338</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The earth-abundant cobalt-catalyzed
-Markovnikov hydroalkylation of unactivated alkenes with oxime esters was achieved by introducing an 8-aminoquinoline directing group on the alkenes. The catalytic system, consisting of commercially available Co(acac)
and PhMeSiH
, enables the construction of unfunctionalized C(sp
)-C(sp
) bonds and features exclusive
-Markovnikov selectivity, good functional group tolerance, and the avoidance of an extra ligand, oxidant, or base. Mechanistic insight into this new catalytic system indicates the involvement of both alkyl radical and cobalt hydride intermediates.</abstract><cop>United States</cop><pmid>32401533</pmid><doi>10.1021/acs.orglett.0c01365</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-3883-2622</orcidid><orcidid>https://orcid.org/0000-0002-1880-8417</orcidid><orcidid>https://orcid.org/0000-0001-8012-4676</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2020-06, Vol.22 (11), p.4333-4338 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2403030293 |
| source | ACS Publications |
| title | Directed Cobalt-Catalyzed anti -Markovnikov Hydroalkylation of Unactivated Alkenes Enabled by "Co-H" Catalysis |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-02T17%3A18%3A34IST&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=Directed%20Cobalt-Catalyzed%20anti%20-Markovnikov%20Hydroalkylation%20of%20Unactivated%20Alkenes%20Enabled%20by%20%22Co-H%22%20Catalysis&rft.jtitle=Organic%20letters&rft.au=Yang,%20Dandan&rft.date=2020-06-05&rft.volume=22&rft.issue=11&rft.spage=4333&rft.epage=4338&rft.pages=4333-4338&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.0c01365&rft_dat=%3Cproquest_cross%3E2403030293%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=2403030293&rft_id=info:pmid/32401533&rfr_iscdi=true |