Intramolecular Nitrene Insertion into Saturated C−H‐Bond‐Mediated C−N Bond Cleavage of a Coordinated NHC Ligand
Ruthenium(II) complexes bearing a tridentate bis(N‐heterocyclic carbene) ligand reacted with iminoiodanes (PhI=NR) resulting in the formation of isolable ruthenium(III)–amido intermediates, which underwent cleavage of a C−N bond of the tridentate ligand and formation of an N‐substituted imine group....
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| Veröffentlicht in: | Chemistry : a European journal 2019-08, Vol.25 (46), p.10828-10833 |
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| container_issue | 46 |
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| container_title | Chemistry : a European journal |
| container_volume | 25 |
| creator | Liu, Yungen Tse, Chun‐Wai Lam, Kar‐Yee Chang, Xiao‐Yong Guan, Xiangguo Chao, Meng‐Yao Huang, Jie‐Sheng Che, Chi‐Ming |
| description | Ruthenium(II) complexes bearing a tridentate bis(N‐heterocyclic carbene) ligand reacted with iminoiodanes (PhI=NR) resulting in the formation of isolable ruthenium(III)–amido intermediates, which underwent cleavage of a C−N bond of the tridentate ligand and formation of an N‐substituted imine group. The RuIII–amido intermediates have been characterized by 1H NMR, UV/Vis, ESI‐MS, and X‐ray crystallography. DFT calculations were performed to provide insight into the reaction mechanism.
N ligands: C−N bond cleavage of a coordinated N‐heterocyclic carbene (NHC), following an intramolecular nitrene C(sp3)−H insertion, has been observed by reaction of PhI=NR with RuII–NHC complexes 1 bearing a tridentate bis(NHC) ligand, resulting in formation of RuII‐imine complexes 2 (see scheme). |
| doi_str_mv | 10.1002/chem.201903012 |
| format | Article |
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N ligands: C−N bond cleavage of a coordinated N‐heterocyclic carbene (NHC), following an intramolecular nitrene C(sp3)−H insertion, has been observed by reaction of PhI=NR with RuII–NHC complexes 1 bearing a tridentate bis(NHC) ligand, resulting in formation of RuII‐imine complexes 2 (see scheme).</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201903012</identifier><identifier>PMID: 31271674</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Chemistry ; Cleavage ; Coordination compounds ; Crystallography ; C−N bond activation ; Intermediates ; Ligands ; N ligands ; N-heterocyclic carbenes ; nitrene transfer reactions ; NMR ; Nuclear magnetic resonance ; Reaction mechanisms ; Ruthenium ; Ruthenium compounds</subject><ispartof>Chemistry : a European journal, 2019-08, Vol.25 (46), p.10828-10833</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4102-c12b7547a7472fdef2058e3cf4400aae63ac92fc683320c5dd9405887b31bd6f3</citedby><cites>FETCH-LOGICAL-c4102-c12b7547a7472fdef2058e3cf4400aae63ac92fc683320c5dd9405887b31bd6f3</cites><orcidid>0000-0003-1724-4362 ; 0000-0003-4538-0548 ; 0000-0003-1394-6164 ; 0000-0002-2554-7219</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%2Fchem.201903012$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201903012$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31271674$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Yungen</creatorcontrib><creatorcontrib>Tse, Chun‐Wai</creatorcontrib><creatorcontrib>Lam, Kar‐Yee</creatorcontrib><creatorcontrib>Chang, Xiao‐Yong</creatorcontrib><creatorcontrib>Guan, Xiangguo</creatorcontrib><creatorcontrib>Chao, Meng‐Yao</creatorcontrib><creatorcontrib>Huang, Jie‐Sheng</creatorcontrib><creatorcontrib>Che, Chi‐Ming</creatorcontrib><title>Intramolecular Nitrene Insertion into Saturated C−H‐Bond‐Mediated C−N Bond Cleavage of a Coordinated NHC Ligand</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>Ruthenium(II) complexes bearing a tridentate bis(N‐heterocyclic carbene) ligand reacted with iminoiodanes (PhI=NR) resulting in the formation of isolable ruthenium(III)–amido intermediates, which underwent cleavage of a C−N bond of the tridentate ligand and formation of an N‐substituted imine group. The RuIII–amido intermediates have been characterized by 1H NMR, UV/Vis, ESI‐MS, and X‐ray crystallography. DFT calculations were performed to provide insight into the reaction mechanism.
N ligands: C−N bond cleavage of a coordinated N‐heterocyclic carbene (NHC), following an intramolecular nitrene C(sp3)−H insertion, has been observed by reaction of PhI=NR with RuII–NHC complexes 1 bearing a tridentate bis(NHC) ligand, resulting in formation of RuII‐imine complexes 2 (see scheme).</description><subject>Chemistry</subject><subject>Cleavage</subject><subject>Coordination compounds</subject><subject>Crystallography</subject><subject>C−N bond activation</subject><subject>Intermediates</subject><subject>Ligands</subject><subject>N ligands</subject><subject>N-heterocyclic carbenes</subject><subject>nitrene transfer reactions</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Reaction mechanisms</subject><subject>Ruthenium</subject><subject>Ruthenium compounds</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqF0T9PGzEYBnCrKiopZWVElrqwXPCf8zke2xNtIoUwUOaTY78HRnc22HcgNsaOVT8in6ROQ1OpS-XhlV793keWHoSOKJlSQtipuYF-yghVhBPK3qAJFYwWXFbiLZoQVcqiElzto_cp3RJCVMX5O7TPKZO0kuUEPS78EHUfOjBjpyNeuSGCB7zwCeLggsfODwFf6mGMegCL65fvP-cvzz8-B2_zOAfrdvsV3mxx3YF-0NeAQ4s1rkOI1vnfaDWv8dJda28_oL1WdwkOX-cBuvpy9q2eF8uLr4v607IwJSWsMJStpSillqVkrYWWETEDbtqyJERrqLg2irWmmnHOiBHWqjKLmVxzurZVyw_QyTb3Lob7EdLQ9C4Z6DrtIYypYUxwTpSoZKYf_6G3YYw-_y4rmZ-gSmQ13SoTQ0oR2uYuul7Hp4aSZlNJs6mk2VWSD45fY8d1D3bH_3SQgdqCR9fB03_imnp-dv43_BcXz5pv</recordid><startdate>20190814</startdate><enddate>20190814</enddate><creator>Liu, Yungen</creator><creator>Tse, Chun‐Wai</creator><creator>Lam, Kar‐Yee</creator><creator>Chang, Xiao‐Yong</creator><creator>Guan, Xiangguo</creator><creator>Chao, Meng‐Yao</creator><creator>Huang, Jie‐Sheng</creator><creator>Che, Chi‐Ming</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-1724-4362</orcidid><orcidid>https://orcid.org/0000-0003-4538-0548</orcidid><orcidid>https://orcid.org/0000-0003-1394-6164</orcidid><orcidid>https://orcid.org/0000-0002-2554-7219</orcidid></search><sort><creationdate>20190814</creationdate><title>Intramolecular Nitrene Insertion into Saturated C−H‐Bond‐Mediated C−N Bond Cleavage of a Coordinated NHC Ligand</title><author>Liu, Yungen ; Tse, Chun‐Wai ; Lam, Kar‐Yee ; Chang, Xiao‐Yong ; Guan, Xiangguo ; Chao, Meng‐Yao ; Huang, Jie‐Sheng ; Che, Chi‐Ming</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4102-c12b7547a7472fdef2058e3cf4400aae63ac92fc683320c5dd9405887b31bd6f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Chemistry</topic><topic>Cleavage</topic><topic>Coordination compounds</topic><topic>Crystallography</topic><topic>C−N bond activation</topic><topic>Intermediates</topic><topic>Ligands</topic><topic>N ligands</topic><topic>N-heterocyclic carbenes</topic><topic>nitrene transfer reactions</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Reaction mechanisms</topic><topic>Ruthenium</topic><topic>Ruthenium compounds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Yungen</creatorcontrib><creatorcontrib>Tse, Chun‐Wai</creatorcontrib><creatorcontrib>Lam, Kar‐Yee</creatorcontrib><creatorcontrib>Chang, Xiao‐Yong</creatorcontrib><creatorcontrib>Guan, Xiangguo</creatorcontrib><creatorcontrib>Chao, Meng‐Yao</creatorcontrib><creatorcontrib>Huang, Jie‐Sheng</creatorcontrib><creatorcontrib>Che, Chi‐Ming</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Yungen</au><au>Tse, Chun‐Wai</au><au>Lam, Kar‐Yee</au><au>Chang, Xiao‐Yong</au><au>Guan, Xiangguo</au><au>Chao, Meng‐Yao</au><au>Huang, Jie‐Sheng</au><au>Che, Chi‐Ming</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Intramolecular Nitrene Insertion into Saturated C−H‐Bond‐Mediated C−N Bond Cleavage of a Coordinated NHC Ligand</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2019-08-14</date><risdate>2019</risdate><volume>25</volume><issue>46</issue><spage>10828</spage><epage>10833</epage><pages>10828-10833</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>Ruthenium(II) complexes bearing a tridentate bis(N‐heterocyclic carbene) ligand reacted with iminoiodanes (PhI=NR) resulting in the formation of isolable ruthenium(III)–amido intermediates, which underwent cleavage of a C−N bond of the tridentate ligand and formation of an N‐substituted imine group. The RuIII–amido intermediates have been characterized by 1H NMR, UV/Vis, ESI‐MS, and X‐ray crystallography. DFT calculations were performed to provide insight into the reaction mechanism.
N ligands: C−N bond cleavage of a coordinated N‐heterocyclic carbene (NHC), following an intramolecular nitrene C(sp3)−H insertion, has been observed by reaction of PhI=NR with RuII–NHC complexes 1 bearing a tridentate bis(NHC) ligand, resulting in formation of RuII‐imine complexes 2 (see scheme).</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>31271674</pmid><doi>10.1002/chem.201903012</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-1724-4362</orcidid><orcidid>https://orcid.org/0000-0003-4538-0548</orcidid><orcidid>https://orcid.org/0000-0003-1394-6164</orcidid><orcidid>https://orcid.org/0000-0002-2554-7219</orcidid></addata></record> |
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| subjects | Chemistry Cleavage Coordination compounds Crystallography C−N bond activation Intermediates Ligands N ligands N-heterocyclic carbenes nitrene transfer reactions NMR Nuclear magnetic resonance Reaction mechanisms Ruthenium Ruthenium compounds |
| title | Intramolecular Nitrene Insertion into Saturated C−H‐Bond‐Mediated C−N Bond Cleavage of a Coordinated NHC Ligand |
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