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Controllable Isomerization of Alkenes by Dual Visible‐Light‐Cobalt Catalysis
We report herein that thermodynamic and kinetic isomerization of alkenes can be accomplished by the combination of visible light with Co catalysis. Utilizing Xantphos as the ligand, the most stable isomers are obtained, while isomerizing terminal alkenes over one position can be selectively controll...
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Published in: | Angewandte Chemie International Edition 2019-04, Vol.58 (17), p.5723-5728 |
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creator | Meng, Qing‐Yuan Schirmer, Tobias E. Katou, Kousuke König, Burkhard |
description | We report herein that thermodynamic and kinetic isomerization of alkenes can be accomplished by the combination of visible light with Co catalysis. Utilizing Xantphos as the ligand, the most stable isomers are obtained, while isomerizing terminal alkenes over one position can be selectively controlled by using DPEphos as the ligand. The presence of the donor–acceptor dye 4CzIPN accelerates the reaction further. Transformation of exocyclic alkenes into the corresponding endocyclic products could be efficiently realized by using 4CzIPN and Co(acac)2 in the absence of any additional ligands. Spectroscopic and spectroelectrochemical investigations indicate CoI being involved in the generation of a Co hydride, which subsequently adds to alkenes initiating the isomerization.
A mild and highly efficient translocation of alkenes by dual visible‐light‐cobalt catalysis has been developed. By the proper choice of ligands, isomerization over one position or more than one position with tolerance of a variety of functional groups can be selectively achieved. |
doi_str_mv | 10.1002/anie.201900849 |
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A mild and highly efficient translocation of alkenes by dual visible‐light‐cobalt catalysis has been developed. By the proper choice of ligands, isomerization over one position or more than one position with tolerance of a variety of functional groups can be selectively achieved.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201900849</identifier><identifier>PMID: 30835931</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>alkene isomerization ; Alkenes ; Catalysis ; Cobalt ; Communication ; Communications ; Isomerization ; Isomers ; Ligands ; photosynthesis ; Stability ; visible light catalysis</subject><ispartof>Angewandte Chemie International Edition, 2019-04, Vol.58 (17), p.5723-5728</ispartof><rights>2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</rights><rights>2019. This article is published under http://creativecommons.org/licenses/by-nc/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5719-3d481da97cad54bb4d8ca553c684b8a712b600827ac6a357feeb84716dd000d63</citedby><cites>FETCH-LOGICAL-c5719-3d481da97cad54bb4d8ca553c684b8a712b600827ac6a357feeb84716dd000d63</cites><orcidid>0000-0002-6131-4850</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.201900849$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201900849$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,315,786,790,891,27957,27958,50923,51032</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30835931$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Meng, Qing‐Yuan</creatorcontrib><creatorcontrib>Schirmer, Tobias E.</creatorcontrib><creatorcontrib>Katou, Kousuke</creatorcontrib><creatorcontrib>König, Burkhard</creatorcontrib><title>Controllable Isomerization of Alkenes by Dual Visible‐Light‐Cobalt Catalysis</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>We report herein that thermodynamic and kinetic isomerization of alkenes can be accomplished by the combination of visible light with Co catalysis. Utilizing Xantphos as the ligand, the most stable isomers are obtained, while isomerizing terminal alkenes over one position can be selectively controlled by using DPEphos as the ligand. The presence of the donor–acceptor dye 4CzIPN accelerates the reaction further. Transformation of exocyclic alkenes into the corresponding endocyclic products could be efficiently realized by using 4CzIPN and Co(acac)2 in the absence of any additional ligands. Spectroscopic and spectroelectrochemical investigations indicate CoI being involved in the generation of a Co hydride, which subsequently adds to alkenes initiating the isomerization.
A mild and highly efficient translocation of alkenes by dual visible‐light‐cobalt catalysis has been developed. By the proper choice of ligands, isomerization over one position or more than one position with tolerance of a variety of functional groups can be selectively achieved.</description><subject>alkene isomerization</subject><subject>Alkenes</subject><subject>Catalysis</subject><subject>Cobalt</subject><subject>Communication</subject><subject>Communications</subject><subject>Isomerization</subject><subject>Isomers</subject><subject>Ligands</subject><subject>photosynthesis</subject><subject>Stability</subject><subject>visible light catalysis</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNqFkctO3DAUhi1Exa3dskSR2HSTwdfY2SCN0gFGGrVdtN1ax4kHDJ6YxgloWPEIPCNPgkdDh9JNV8eSP3_yf36EDgkeEYzpCbTOjigmJcaKl1tojwhKciYl205nzlgulSC7aD_G68QrhYsdtMuwYqJkZA99r0Lbd8F7MN5m0xgWtnMP0LvQZmGejf2NbW3MzDL7MoDPfrnoEvj8-DRzl1d9mlUw4Pusgh78Mrr4EX2Yg4_20-s8QD_PJj-qi3z27XxajWd5LSQpc9ZwRRooZQ2N4MbwRtUgBKsLxY0CSagpUiQqoS6ACTm31iguSdE0GOOmYAfodO29HczCNrVNMcDr284toFvqAE6_v2ndlb4Md7oQpGRyJfj8KujC78HGXi9crG3aRGvDEDUlSgklOcMJPf4HvQ5D16Z4mlIsKOcCi0SN1lTdhRg7O998hmC9KkuvytKbstKDo78jbPA_7SSgXAP3ztvlf3R6_HU6eZO_ADT_o4A</recordid><startdate>20190416</startdate><enddate>20190416</enddate><creator>Meng, Qing‐Yuan</creator><creator>Schirmer, Tobias E.</creator><creator>Katou, Kousuke</creator><creator>König, Burkhard</creator><general>Wiley Subscription Services, Inc</general><general>John Wiley and Sons Inc</general><scope>24P</scope><scope>WIN</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/0000-0002-6131-4850</orcidid></search><sort><creationdate>20190416</creationdate><title>Controllable Isomerization of Alkenes by Dual Visible‐Light‐Cobalt Catalysis</title><author>Meng, Qing‐Yuan ; Schirmer, Tobias E. ; Katou, Kousuke ; König, Burkhard</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5719-3d481da97cad54bb4d8ca553c684b8a712b600827ac6a357feeb84716dd000d63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>alkene isomerization</topic><topic>Alkenes</topic><topic>Catalysis</topic><topic>Cobalt</topic><topic>Communication</topic><topic>Communications</topic><topic>Isomerization</topic><topic>Isomers</topic><topic>Ligands</topic><topic>photosynthesis</topic><topic>Stability</topic><topic>visible light catalysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Meng, Qing‐Yuan</creatorcontrib><creatorcontrib>Schirmer, Tobias E.</creatorcontrib><creatorcontrib>Katou, Kousuke</creatorcontrib><creatorcontrib>König, Burkhard</creatorcontrib><collection>Wiley Online Library Open Access</collection><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>Meng, Qing‐Yuan</au><au>Schirmer, Tobias E.</au><au>Katou, Kousuke</au><au>König, Burkhard</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Controllable Isomerization of Alkenes by Dual Visible‐Light‐Cobalt Catalysis</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2019-04-16</date><risdate>2019</risdate><volume>58</volume><issue>17</issue><spage>5723</spage><epage>5728</epage><pages>5723-5728</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><notes>ObjectType-Article-1</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-2</notes><notes>content type line 23</notes><abstract>We report herein that thermodynamic and kinetic isomerization of alkenes can be accomplished by the combination of visible light with Co catalysis. Utilizing Xantphos as the ligand, the most stable isomers are obtained, while isomerizing terminal alkenes over one position can be selectively controlled by using DPEphos as the ligand. The presence of the donor–acceptor dye 4CzIPN accelerates the reaction further. Transformation of exocyclic alkenes into the corresponding endocyclic products could be efficiently realized by using 4CzIPN and Co(acac)2 in the absence of any additional ligands. Spectroscopic and spectroelectrochemical investigations indicate CoI being involved in the generation of a Co hydride, which subsequently adds to alkenes initiating the isomerization.
A mild and highly efficient translocation of alkenes by dual visible‐light‐cobalt catalysis has been developed. By the proper choice of ligands, isomerization over one position or more than one position with tolerance of a variety of functional groups can be selectively achieved.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>30835931</pmid><doi>10.1002/anie.201900849</doi><tpages>6</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-6131-4850</orcidid><oa>free_for_read</oa></addata></record> |
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subjects | alkene isomerization Alkenes Catalysis Cobalt Communication Communications Isomerization Isomers Ligands photosynthesis Stability visible light catalysis |
title | Controllable Isomerization of Alkenes by Dual Visible‐Light‐Cobalt Catalysis |
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