Selective C(sp3)−H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow
A mild and selective C(sp3)−H aerobic oxidation enabled by decatungstate photocatalysis has been developed. The reaction can be significantly improved in a microflow reactor enabling the safe use of oxygen and enhanced irradiation of the reaction mixture. Our method allows for the oxidation of both...
Gespeichert in:
| Veröffentlicht in: | Angewandte Chemie International Edition 2018-04, Vol.57 (15), p.4078-4082 |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 4082 |
|---|---|
| container_issue | 15 |
| container_start_page | 4078 |
| container_title | Angewandte Chemie International Edition |
| container_volume | 57 |
| creator | Laudadio, Gabriele Govaerts, Sebastian Wang, Ying Ravelli, Davide Koolman, Hannes F. Fagnoni, Maurizio Djuric, Stevan W. Noël, Timothy |
| description | A mild and selective C(sp3)−H aerobic oxidation enabled by decatungstate photocatalysis has been developed. The reaction can be significantly improved in a microflow reactor enabling the safe use of oxygen and enhanced irradiation of the reaction mixture. Our method allows for the oxidation of both activated and unactivated C−H bonds (30 examples). The ability to selectively oxidize natural scaffolds, such as (−)‐ambroxide, pregnenolone acetate, (+)‐sclareolide, and artemisinin, exemplifies the utility of this new method.
Good clean functionalization: A mild and selective C(sp3)−H oxidation promoted by an inexpensive decatungstate photocatalyst was significantly improved by a microflow reactor, which enabled the safe use of oxygen and enhanced irradiation of the reaction mixture. Both activated and unactivated C−H bonds could be oxidized by this sustainable method, including those in natural scaffolds, such as (−)‐ambroxide and artemisinin. |
| doi_str_mv | 10.1002/anie.201800818 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_5900731</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2003039935</sourcerecordid><originalsourceid>FETCH-LOGICAL-c5718-e3dfb1e94040218e7e5e58764280c5aa527f7b597e34f1e0db8ac9433130d33c3</originalsourceid><addsrcrecordid>eNqFkU1PFDEYxxujEVi8ejRNvMBh1r5MaXsx2ayLkBAwQb02nc4zUNJtl-kMuN_Asx_RT2LJwvpy8dQn7e_5pf_8EXpNyZQSwt7Z6GHKCFWEKKqeoV0qGK24lPx5mWvOK6kE3UF7Od8UXily9BLtMF0LKpnYRV8vIYAb_B3g-UFe8cOf33-c4Bn0qfEOX3zzrR18ingRbROgxc0afwBnhzFe5cEOgD9dpyGVCxvW2WfsIz4O6X4fvehsyPDq8ZygL8eLz_OT6uzi4-l8dlY5IamqgLddQ0HXpCaMKpAgQCh5VDNFnLBWMNnJRmgJvO4okLZR1umSinLScu74BL3feFdjs4TWQRx6G8yq90vbr02y3vz9Ev21uUp3RmhCZNFM0MGjoE-3I-TBLH12EIKNkMZsGCGccK25KOjbf9CbNPaxxCsUlZorTlWhphvK9SnnHrrtZygxD5WZh8rMtrKy8ObPCFv8qaMC6A1w7wOs_6Mzs_PTxW_5L90Co0A</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2017938318</pqid></control><display><type>article</type><title>Selective C(sp3)−H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Laudadio, Gabriele ; Govaerts, Sebastian ; Wang, Ying ; Ravelli, Davide ; Koolman, Hannes F. ; Fagnoni, Maurizio ; Djuric, Stevan W. ; Noël, Timothy</creator><creatorcontrib>Laudadio, Gabriele ; Govaerts, Sebastian ; Wang, Ying ; Ravelli, Davide ; Koolman, Hannes F. ; Fagnoni, Maurizio ; Djuric, Stevan W. ; Noël, Timothy</creatorcontrib><description>A mild and selective C(sp3)−H aerobic oxidation enabled by decatungstate photocatalysis has been developed. The reaction can be significantly improved in a microflow reactor enabling the safe use of oxygen and enhanced irradiation of the reaction mixture. Our method allows for the oxidation of both activated and unactivated C−H bonds (30 examples). The ability to selectively oxidize natural scaffolds, such as (−)‐ambroxide, pregnenolone acetate, (+)‐sclareolide, and artemisinin, exemplifies the utility of this new method.
Good clean functionalization: A mild and selective C(sp3)−H oxidation promoted by an inexpensive decatungstate photocatalyst was significantly improved by a microflow reactor, which enabled the safe use of oxygen and enhanced irradiation of the reaction mixture. Both activated and unactivated C−H bonds could be oxidized by this sustainable method, including those in natural scaffolds, such as (−)‐ambroxide and artemisinin.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201800818</identifier><identifier>PMID: 29451725</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Acetic acid ; aerobic oxidation ; Artemisinin ; C(sp3)−H functionalization ; Communication ; Communications ; decatungstate ; flow chemistry ; Irradiation ; Oxidation ; Photocatalysis ; Pregnenolone ; Radiation</subject><ispartof>Angewandte Chemie International Edition, 2018-04, Vol.57 (15), p.4078-4082</ispartof><rights>2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</rights><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5718-e3dfb1e94040218e7e5e58764280c5aa527f7b597e34f1e0db8ac9433130d33c3</citedby><cites>FETCH-LOGICAL-c5718-e3dfb1e94040218e7e5e58764280c5aa527f7b597e34f1e0db8ac9433130d33c3</cites><orcidid>0000-0003-2201-4828 ; 0000-0002-0742-9243 ; 0000-0002-2749-8393 ; 0000-0003-0247-7585 ; 0000-0002-3107-6927</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.201800818$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201800818$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,776,780,881,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29451725$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Laudadio, Gabriele</creatorcontrib><creatorcontrib>Govaerts, Sebastian</creatorcontrib><creatorcontrib>Wang, Ying</creatorcontrib><creatorcontrib>Ravelli, Davide</creatorcontrib><creatorcontrib>Koolman, Hannes F.</creatorcontrib><creatorcontrib>Fagnoni, Maurizio</creatorcontrib><creatorcontrib>Djuric, Stevan W.</creatorcontrib><creatorcontrib>Noël, Timothy</creatorcontrib><title>Selective C(sp3)−H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>A mild and selective C(sp3)−H aerobic oxidation enabled by decatungstate photocatalysis has been developed. The reaction can be significantly improved in a microflow reactor enabling the safe use of oxygen and enhanced irradiation of the reaction mixture. Our method allows for the oxidation of both activated and unactivated C−H bonds (30 examples). The ability to selectively oxidize natural scaffolds, such as (−)‐ambroxide, pregnenolone acetate, (+)‐sclareolide, and artemisinin, exemplifies the utility of this new method.
Good clean functionalization: A mild and selective C(sp3)−H oxidation promoted by an inexpensive decatungstate photocatalyst was significantly improved by a microflow reactor, which enabled the safe use of oxygen and enhanced irradiation of the reaction mixture. Both activated and unactivated C−H bonds could be oxidized by this sustainable method, including those in natural scaffolds, such as (−)‐ambroxide and artemisinin.</description><subject>Acetic acid</subject><subject>aerobic oxidation</subject><subject>Artemisinin</subject><subject>C(sp3)−H functionalization</subject><subject>Communication</subject><subject>Communications</subject><subject>decatungstate</subject><subject>flow chemistry</subject><subject>Irradiation</subject><subject>Oxidation</subject><subject>Photocatalysis</subject><subject>Pregnenolone</subject><subject>Radiation</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><recordid>eNqFkU1PFDEYxxujEVi8ejRNvMBh1r5MaXsx2ayLkBAwQb02nc4zUNJtl-kMuN_Asx_RT2LJwvpy8dQn7e_5pf_8EXpNyZQSwt7Z6GHKCFWEKKqeoV0qGK24lPx5mWvOK6kE3UF7Od8UXily9BLtMF0LKpnYRV8vIYAb_B3g-UFe8cOf33-c4Bn0qfEOX3zzrR18ingRbROgxc0afwBnhzFe5cEOgD9dpyGVCxvW2WfsIz4O6X4fvehsyPDq8ZygL8eLz_OT6uzi4-l8dlY5IamqgLddQ0HXpCaMKpAgQCh5VDNFnLBWMNnJRmgJvO4okLZR1umSinLScu74BL3feFdjs4TWQRx6G8yq90vbr02y3vz9Ev21uUp3RmhCZNFM0MGjoE-3I-TBLH12EIKNkMZsGCGccK25KOjbf9CbNPaxxCsUlZorTlWhphvK9SnnHrrtZygxD5WZh8rMtrKy8ObPCFv8qaMC6A1w7wOs_6Mzs_PTxW_5L90Co0A</recordid><startdate>20180403</startdate><enddate>20180403</enddate><creator>Laudadio, Gabriele</creator><creator>Govaerts, Sebastian</creator><creator>Wang, Ying</creator><creator>Ravelli, Davide</creator><creator>Koolman, Hannes F.</creator><creator>Fagnoni, Maurizio</creator><creator>Djuric, Stevan W.</creator><creator>Noël, Timothy</creator><general>Wiley Subscription Services, Inc</general><general>John Wiley and Sons Inc</general><scope>24P</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0003-2201-4828</orcidid><orcidid>https://orcid.org/0000-0002-0742-9243</orcidid><orcidid>https://orcid.org/0000-0002-2749-8393</orcidid><orcidid>https://orcid.org/0000-0003-0247-7585</orcidid><orcidid>https://orcid.org/0000-0002-3107-6927</orcidid></search><sort><creationdate>20180403</creationdate><title>Selective C(sp3)−H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow</title><author>Laudadio, Gabriele ; Govaerts, Sebastian ; Wang, Ying ; Ravelli, Davide ; Koolman, Hannes F. ; Fagnoni, Maurizio ; Djuric, Stevan W. ; Noël, Timothy</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5718-e3dfb1e94040218e7e5e58764280c5aa527f7b597e34f1e0db8ac9433130d33c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Acetic acid</topic><topic>aerobic oxidation</topic><topic>Artemisinin</topic><topic>C(sp3)−H functionalization</topic><topic>Communication</topic><topic>Communications</topic><topic>decatungstate</topic><topic>flow chemistry</topic><topic>Irradiation</topic><topic>Oxidation</topic><topic>Photocatalysis</topic><topic>Pregnenolone</topic><topic>Radiation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Laudadio, Gabriele</creatorcontrib><creatorcontrib>Govaerts, Sebastian</creatorcontrib><creatorcontrib>Wang, Ying</creatorcontrib><creatorcontrib>Ravelli, Davide</creatorcontrib><creatorcontrib>Koolman, Hannes F.</creatorcontrib><creatorcontrib>Fagnoni, Maurizio</creatorcontrib><creatorcontrib>Djuric, Stevan W.</creatorcontrib><creatorcontrib>Noël, Timothy</creatorcontrib><collection>Wiley Online Library Open Access</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</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>Laudadio, Gabriele</au><au>Govaerts, Sebastian</au><au>Wang, Ying</au><au>Ravelli, Davide</au><au>Koolman, Hannes F.</au><au>Fagnoni, Maurizio</au><au>Djuric, Stevan W.</au><au>Noël, Timothy</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Selective C(sp3)−H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2018-04-03</date><risdate>2018</risdate><volume>57</volume><issue>15</issue><spage>4078</spage><epage>4082</epage><pages>4078-4082</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>A mild and selective C(sp3)−H aerobic oxidation enabled by decatungstate photocatalysis has been developed. The reaction can be significantly improved in a microflow reactor enabling the safe use of oxygen and enhanced irradiation of the reaction mixture. Our method allows for the oxidation of both activated and unactivated C−H bonds (30 examples). The ability to selectively oxidize natural scaffolds, such as (−)‐ambroxide, pregnenolone acetate, (+)‐sclareolide, and artemisinin, exemplifies the utility of this new method.
Good clean functionalization: A mild and selective C(sp3)−H oxidation promoted by an inexpensive decatungstate photocatalyst was significantly improved by a microflow reactor, which enabled the safe use of oxygen and enhanced irradiation of the reaction mixture. Both activated and unactivated C−H bonds could be oxidized by this sustainable method, including those in natural scaffolds, such as (−)‐ambroxide and artemisinin.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>29451725</pmid><doi>10.1002/anie.201800818</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0003-2201-4828</orcidid><orcidid>https://orcid.org/0000-0002-0742-9243</orcidid><orcidid>https://orcid.org/0000-0002-2749-8393</orcidid><orcidid>https://orcid.org/0000-0003-0247-7585</orcidid><orcidid>https://orcid.org/0000-0002-3107-6927</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie International Edition, 2018-04, Vol.57 (15), p.4078-4082 |
| issn | 1433-7851 1521-3773 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_5900731 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Acetic acid aerobic oxidation Artemisinin C(sp3)−H functionalization Communication Communications decatungstate flow chemistry Irradiation Oxidation Photocatalysis Pregnenolone Radiation |
| title | Selective C(sp3)−H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-09T00%3A45%3A49IST&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=Selective%20C(sp3)%E2%88%92H%20Aerobic%20Oxidation%20Enabled%20by%20Decatungstate%20Photocatalysis%20in%20Flow&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Laudadio,%20Gabriele&rft.date=2018-04-03&rft.volume=57&rft.issue=15&rft.spage=4078&rft.epage=4082&rft.pages=4078-4082&rft.issn=1433-7851&rft.eissn=1521-3773&rft_id=info:doi/10.1002/anie.201800818&rft_dat=%3Cproquest_pubme%3E2003039935%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=2017938318&rft_id=info:pmid/29451725&rfr_iscdi=true |