External oxidant-compatible phosphorus(III)-directed site-selective C-H carbonylation
The first development of an external oxidant-compatible system involving a phosphorus(III)-directed C-H functionalization has been uncovered. An efficient C-H esterification of indoles with CO and alcohols has been reported in which the high reactivity and the exclusive C7-selectivity derives from t...
Gespeichert in:
| Veröffentlicht in: | Science advances 2020-12, Vol.6 (51) |
|---|---|
| Hauptverfasser: | , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | |
|---|---|
| container_issue | 51 |
| container_start_page | |
| container_title | Science advances |
| container_volume | 6 |
| creator | Dong, Ben Qian, Jiasheng Li, Mingjie Wang, Zheng-Jun Wang, Minyan Wang, Dingyi Yuan, Chengkai Han, Ying Zhao, Yue Shi, Zhuangzhi |
| description | The first development of an external oxidant-compatible system involving a phosphorus(III)-directed C-H functionalization has been uncovered. An efficient C-H esterification of indoles with CO and alcohols has been reported in which the high reactivity and the exclusive C7-selectivity derives from the selection of a P(III)-directing group and the utilization of benzoquinone as an external oxidant with palladium catalysis. This strategy shows many advantages, involving an easily accessible and removable directing group, the use of cheap carbonylation sources, a broad substrate scope, and excellent positional selectivity. Two cyclopalladated intermediates were confirmed by x-ray analysis, uncovering key mechanistic features of this P(III)-directed C-H metalation event. |
| doi_str_mv | 10.1126/sciadv.abd1378 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_7744084</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2470902975</sourcerecordid><originalsourceid>FETCH-LOGICAL-c456t-500dcfa29ef35d5e2d548a3f23646619dedc2b25eca26a66e7d1c0e46e8fbf273</originalsourceid><addsrcrecordid>eNpVUU1PAjEQbYxGCHL1aPaIh8V-bLu7FxNDUEhIvMi56bazUrNssV0I_HtrQIKHycxk3rx5mYfQPcFjQqh4CtoqsxuryhCWF1eoT1nOU8qz4vqi7qFhCF8YY5IJwUl5i3qMMVpQxvtoOd134FvVJG5vjWq7VLv1RnW2aiDZrFyI4bdhNJ_PH1NjPegOTBJsB2mAJnZ2B8kknSVa-cq1hyauuvYO3dSqCTA85QFavk4_JrN08f42n7wsUp1x0aUcY6NrRUuoGTccqIlyFaspE1EqKQ0YTSvKQSsqlBCQG6IxZAKKuqppzgbo-ci72VbrCIa286qRG2_Xyh-kU1b-n7R2JT_dTuZ5luEiiwSjE4F331sInVzboKFpVAtuGyTNclxiWuY8QsdHqPYuBA_1-QzB8tcOebRDnuyICw-X4s7wv-ezH3Kfipg</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2470902975</pqid></control><display><type>article</type><title>External oxidant-compatible phosphorus(III)-directed site-selective C-H carbonylation</title><source>DOAJ Directory of Open Access Journals</source><source>EZB-FREE-00999 freely available EZB journals</source><source>PubMed Central</source><creator>Dong, Ben ; Qian, Jiasheng ; Li, Mingjie ; Wang, Zheng-Jun ; Wang, Minyan ; Wang, Dingyi ; Yuan, Chengkai ; Han, Ying ; Zhao, Yue ; Shi, Zhuangzhi</creator><creatorcontrib>Dong, Ben ; Qian, Jiasheng ; Li, Mingjie ; Wang, Zheng-Jun ; Wang, Minyan ; Wang, Dingyi ; Yuan, Chengkai ; Han, Ying ; Zhao, Yue ; Shi, Zhuangzhi</creatorcontrib><description>The first development of an external oxidant-compatible system involving a phosphorus(III)-directed C-H functionalization has been uncovered. An efficient C-H esterification of indoles with CO and alcohols has been reported in which the high reactivity and the exclusive C7-selectivity derives from the selection of a P(III)-directing group and the utilization of benzoquinone as an external oxidant with palladium catalysis. This strategy shows many advantages, involving an easily accessible and removable directing group, the use of cheap carbonylation sources, a broad substrate scope, and excellent positional selectivity. Two cyclopalladated intermediates were confirmed by x-ray analysis, uncovering key mechanistic features of this P(III)-directed C-H metalation event.</description><identifier>ISSN: 2375-2548</identifier><identifier>EISSN: 2375-2548</identifier><identifier>DOI: 10.1126/sciadv.abd1378</identifier><identifier>PMID: 33328235</identifier><language>eng</language><publisher>United States: American Association for the Advancement of Science</publisher><subject>Chemistry ; Organic Chemistry ; SciAdv r-articles</subject><ispartof>Science advances, 2020-12, Vol.6 (51)</ispartof><rights>Copyright © 2020 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. No claim to original U.S. Government Works. Distributed under a Creative Commons Attribution NonCommercial License 4.0 (CC BY-NC).</rights><rights>Copyright © 2020 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. No claim to original U.S. Government Works. Distributed under a Creative Commons Attribution NonCommercial License 4.0 (CC BY-NC). 2020 The Authors</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c456t-500dcfa29ef35d5e2d548a3f23646619dedc2b25eca26a66e7d1c0e46e8fbf273</citedby><cites>FETCH-LOGICAL-c456t-500dcfa29ef35d5e2d548a3f23646619dedc2b25eca26a66e7d1c0e46e8fbf273</cites><orcidid>0000-0001-6094-4087 ; 0000-0003-0103-4088 ; 0000-0001-7241-0699 ; 0000-0003-3896-5986 ; 0000-0003-1789-5683 ; 0000-0001-6652-493X ; 0000-0003-4571-4413</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/PMC7744084/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC7744084/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33328235$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Dong, Ben</creatorcontrib><creatorcontrib>Qian, Jiasheng</creatorcontrib><creatorcontrib>Li, Mingjie</creatorcontrib><creatorcontrib>Wang, Zheng-Jun</creatorcontrib><creatorcontrib>Wang, Minyan</creatorcontrib><creatorcontrib>Wang, Dingyi</creatorcontrib><creatorcontrib>Yuan, Chengkai</creatorcontrib><creatorcontrib>Han, Ying</creatorcontrib><creatorcontrib>Zhao, Yue</creatorcontrib><creatorcontrib>Shi, Zhuangzhi</creatorcontrib><title>External oxidant-compatible phosphorus(III)-directed site-selective C-H carbonylation</title><title>Science advances</title><addtitle>Sci Adv</addtitle><description>The first development of an external oxidant-compatible system involving a phosphorus(III)-directed C-H functionalization has been uncovered. An efficient C-H esterification of indoles with CO and alcohols has been reported in which the high reactivity and the exclusive C7-selectivity derives from the selection of a P(III)-directing group and the utilization of benzoquinone as an external oxidant with palladium catalysis. This strategy shows many advantages, involving an easily accessible and removable directing group, the use of cheap carbonylation sources, a broad substrate scope, and excellent positional selectivity. Two cyclopalladated intermediates were confirmed by x-ray analysis, uncovering key mechanistic features of this P(III)-directed C-H metalation event.</description><subject>Chemistry</subject><subject>Organic Chemistry</subject><subject>SciAdv r-articles</subject><issn>2375-2548</issn><issn>2375-2548</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNpVUU1PAjEQbYxGCHL1aPaIh8V-bLu7FxNDUEhIvMi56bazUrNssV0I_HtrQIKHycxk3rx5mYfQPcFjQqh4CtoqsxuryhCWF1eoT1nOU8qz4vqi7qFhCF8YY5IJwUl5i3qMMVpQxvtoOd134FvVJG5vjWq7VLv1RnW2aiDZrFyI4bdhNJ_PH1NjPegOTBJsB2mAJnZ2B8kknSVa-cq1hyauuvYO3dSqCTA85QFavk4_JrN08f42n7wsUp1x0aUcY6NrRUuoGTccqIlyFaspE1EqKQ0YTSvKQSsqlBCQG6IxZAKKuqppzgbo-ci72VbrCIa286qRG2_Xyh-kU1b-n7R2JT_dTuZ5luEiiwSjE4F331sInVzboKFpVAtuGyTNclxiWuY8QsdHqPYuBA_1-QzB8tcOebRDnuyICw-X4s7wv-ezH3Kfipg</recordid><startdate>20201201</startdate><enddate>20201201</enddate><creator>Dong, Ben</creator><creator>Qian, Jiasheng</creator><creator>Li, Mingjie</creator><creator>Wang, Zheng-Jun</creator><creator>Wang, Minyan</creator><creator>Wang, Dingyi</creator><creator>Yuan, Chengkai</creator><creator>Han, Ying</creator><creator>Zhao, Yue</creator><creator>Shi, Zhuangzhi</creator><general>American Association for the Advancement of Science</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-6094-4087</orcidid><orcidid>https://orcid.org/0000-0003-0103-4088</orcidid><orcidid>https://orcid.org/0000-0001-7241-0699</orcidid><orcidid>https://orcid.org/0000-0003-3896-5986</orcidid><orcidid>https://orcid.org/0000-0003-1789-5683</orcidid><orcidid>https://orcid.org/0000-0001-6652-493X</orcidid><orcidid>https://orcid.org/0000-0003-4571-4413</orcidid></search><sort><creationdate>20201201</creationdate><title>External oxidant-compatible phosphorus(III)-directed site-selective C-H carbonylation</title><author>Dong, Ben ; Qian, Jiasheng ; Li, Mingjie ; Wang, Zheng-Jun ; Wang, Minyan ; Wang, Dingyi ; Yuan, Chengkai ; Han, Ying ; Zhao, Yue ; Shi, Zhuangzhi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c456t-500dcfa29ef35d5e2d548a3f23646619dedc2b25eca26a66e7d1c0e46e8fbf273</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Chemistry</topic><topic>Organic Chemistry</topic><topic>SciAdv r-articles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dong, Ben</creatorcontrib><creatorcontrib>Qian, Jiasheng</creatorcontrib><creatorcontrib>Li, Mingjie</creatorcontrib><creatorcontrib>Wang, Zheng-Jun</creatorcontrib><creatorcontrib>Wang, Minyan</creatorcontrib><creatorcontrib>Wang, Dingyi</creatorcontrib><creatorcontrib>Yuan, Chengkai</creatorcontrib><creatorcontrib>Han, Ying</creatorcontrib><creatorcontrib>Zhao, Yue</creatorcontrib><creatorcontrib>Shi, Zhuangzhi</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Science advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dong, Ben</au><au>Qian, Jiasheng</au><au>Li, Mingjie</au><au>Wang, Zheng-Jun</au><au>Wang, Minyan</au><au>Wang, Dingyi</au><au>Yuan, Chengkai</au><au>Han, Ying</au><au>Zhao, Yue</au><au>Shi, Zhuangzhi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>External oxidant-compatible phosphorus(III)-directed site-selective C-H carbonylation</atitle><jtitle>Science advances</jtitle><addtitle>Sci Adv</addtitle><date>2020-12-01</date><risdate>2020</risdate><volume>6</volume><issue>51</issue><issn>2375-2548</issn><eissn>2375-2548</eissn><abstract>The first development of an external oxidant-compatible system involving a phosphorus(III)-directed C-H functionalization has been uncovered. An efficient C-H esterification of indoles with CO and alcohols has been reported in which the high reactivity and the exclusive C7-selectivity derives from the selection of a P(III)-directing group and the utilization of benzoquinone as an external oxidant with palladium catalysis. This strategy shows many advantages, involving an easily accessible and removable directing group, the use of cheap carbonylation sources, a broad substrate scope, and excellent positional selectivity. Two cyclopalladated intermediates were confirmed by x-ray analysis, uncovering key mechanistic features of this P(III)-directed C-H metalation event.</abstract><cop>United States</cop><pub>American Association for the Advancement of Science</pub><pmid>33328235</pmid><doi>10.1126/sciadv.abd1378</doi><orcidid>https://orcid.org/0000-0001-6094-4087</orcidid><orcidid>https://orcid.org/0000-0003-0103-4088</orcidid><orcidid>https://orcid.org/0000-0001-7241-0699</orcidid><orcidid>https://orcid.org/0000-0003-3896-5986</orcidid><orcidid>https://orcid.org/0000-0003-1789-5683</orcidid><orcidid>https://orcid.org/0000-0001-6652-493X</orcidid><orcidid>https://orcid.org/0000-0003-4571-4413</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2375-2548 |
| ispartof | Science advances, 2020-12, Vol.6 (51) |
| issn | 2375-2548 2375-2548 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_7744084 |
| source | DOAJ Directory of Open Access Journals; EZB-FREE-00999 freely available EZB journals; PubMed Central |
| subjects | Chemistry Organic Chemistry SciAdv r-articles |
| title | External oxidant-compatible phosphorus(III)-directed site-selective C-H carbonylation |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-01T01%3A05%3A38IST&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=External%20oxidant-compatible%20phosphorus(III)-directed%20site-selective%20C-H%20carbonylation&rft.jtitle=Science%20advances&rft.au=Dong,%20Ben&rft.date=2020-12-01&rft.volume=6&rft.issue=51&rft.issn=2375-2548&rft.eissn=2375-2548&rft_id=info:doi/10.1126/sciadv.abd1378&rft_dat=%3Cproquest_pubme%3E2470902975%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=2470902975&rft_id=info:pmid/33328235&rfr_iscdi=true |