Efficient alkene hydrosilation with bis(8-quinolyl)phosphine (NPN) nickel catalysts. The dominant role of silyl-over hydrido-nickel catalytic intermediates
A cationic nickel complex of the bis(8-quinolyl)(3,5-di- tert -butylphenoxy)phosphine (NPN) ligand, [(NPN)NiCl] + , is a precursor to efficient catalysts for the hydrosilation of alkenes with a variety of hydrosilanes under mild conditions and low catalyst loadings. DFT studies reveal the presence o...
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| Veröffentlicht in: | Chemical science (Cambridge) 2020-05, Vol.11 (19), p.543-551 |
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| creator | Yang, Jian Postils, Verònica Lipschutz, Michael I Fasulo, Meg Raynaud, Christophe Clot, Eric Eisenstein, Odile Tilley, T. Don |
| description | A cationic nickel complex of the bis(8-quinolyl)(3,5-di-
tert
-butylphenoxy)phosphine (NPN) ligand, [(NPN)NiCl]
+
, is a precursor to efficient catalysts for the hydrosilation of alkenes with a variety of hydrosilanes under mild conditions and low catalyst loadings. DFT studies reveal the presence of two coupled catalytic cycles based on [(NPN)NiH]
+
and [(NPN)NiSiR
3
]
+
active species, with the latter being more efficient for producing the product. The preferred silyl-based catalysis is not due to a more facile insertion of alkene into the Ni-Si (
vs.
Ni-H) bond, but by consistent and efficient conversions of the hydride to the silyl complex.
A cationic nickel complex of the bis(8-quinolyl)(3,5-di-
tert
-butylphenoxy)phosphine (NPN) ligand, [(NPN)NiCl]
+
, is a precursor to efficient catalysts for the hydrosilation of alkenes with hydrosilanes under mild conditions and low catalyst loadings. |
| doi_str_mv | 10.1039/d0sc00997k |
| format | Article |
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tert
-butylphenoxy)phosphine (NPN) ligand, [(NPN)NiCl]
+
, is a precursor to efficient catalysts for the hydrosilation of alkenes with a variety of hydrosilanes under mild conditions and low catalyst loadings. DFT studies reveal the presence of two coupled catalytic cycles based on [(NPN)NiH]
+
and [(NPN)NiSiR
3
]
+
active species, with the latter being more efficient for producing the product. The preferred silyl-based catalysis is not due to a more facile insertion of alkene into the Ni-Si (
vs.
Ni-H) bond, but by consistent and efficient conversions of the hydride to the silyl complex.
A cationic nickel complex of the bis(8-quinolyl)(3,5-di-
tert
-butylphenoxy)phosphine (NPN) ligand, [(NPN)NiCl]
+
, is a precursor to efficient catalysts for the hydrosilation of alkenes with hydrosilanes under mild conditions and low catalyst loadings.</description><identifier>ISSN: 2041-6520</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/d0sc00997k</identifier><identifier>PMID: 34122961</identifier><language>eng</language><publisher>CAMBRIDGE: Royal Soc Chemistry</publisher><subject>Alkenes ; Catalysis ; Catalysts ; Chemical reactions ; Chemical Sciences ; Chemistry ; Chemistry, Multidisciplinary ; Crystallography ; Inorganic chemistry ; Mathematical analysis ; Nickel ; or physical chemistry ; Phosphines ; Physical Sciences ; Science & Technology ; Theoretical and</subject><ispartof>Chemical science (Cambridge), 2020-05, Vol.11 (19), p.543-551</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2020</rights><rights>info:eu-repo/semantics/openAccess</rights><rights>Attribution</rights><rights>This journal is © The Royal Society of Chemistry 2020 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>true</woscitedreferencessubscribed><woscitedreferencescount>9</woscitedreferencescount><woscitedreferencesoriginalsourcerecordid>wos000536688300020</woscitedreferencesoriginalsourcerecordid><citedby>FETCH-LOGICAL-c512t-db4d6ce9fa717d154147e74be6ca80a6612c575e5d133b180aae9ed633a475f73</citedby><cites>FETCH-LOGICAL-c512t-db4d6ce9fa717d154147e74be6ca80a6612c575e5d133b180aae9ed633a475f73</cites><orcidid>0000-0001-8332-5545 ; 0000-0003-0979-2051 ; 0000-0002-6671-9099 ; 0000-0002-7467-9277 ; 0000-0001-5056-0311 ; 0000-0002-9960-0633</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/PMC8159242/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8159242/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,864,885,2114,26567,27924,27925,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34122961$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.umontpellier.fr/hal-02617107$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Yang, Jian</creatorcontrib><creatorcontrib>Postils, Verònica</creatorcontrib><creatorcontrib>Lipschutz, Michael I</creatorcontrib><creatorcontrib>Fasulo, Meg</creatorcontrib><creatorcontrib>Raynaud, Christophe</creatorcontrib><creatorcontrib>Clot, Eric</creatorcontrib><creatorcontrib>Eisenstein, Odile</creatorcontrib><creatorcontrib>Tilley, T. Don</creatorcontrib><title>Efficient alkene hydrosilation with bis(8-quinolyl)phosphine (NPN) nickel catalysts. The dominant role of silyl-over hydrido-nickel catalytic intermediates</title><title>Chemical science (Cambridge)</title><addtitle>CHEM SCI</addtitle><addtitle>Chem Sci</addtitle><description>A cationic nickel complex of the bis(8-quinolyl)(3,5-di-
tert
-butylphenoxy)phosphine (NPN) ligand, [(NPN)NiCl]
+
, is a precursor to efficient catalysts for the hydrosilation of alkenes with a variety of hydrosilanes under mild conditions and low catalyst loadings. DFT studies reveal the presence of two coupled catalytic cycles based on [(NPN)NiH]
+
and [(NPN)NiSiR
3
]
+
active species, with the latter being more efficient for producing the product. The preferred silyl-based catalysis is not due to a more facile insertion of alkene into the Ni-Si (
vs.
Ni-H) bond, but by consistent and efficient conversions of the hydride to the silyl complex.
A cationic nickel complex of the bis(8-quinolyl)(3,5-di-
tert
-butylphenoxy)phosphine (NPN) ligand, [(NPN)NiCl]
+
, is a precursor to efficient catalysts for the hydrosilation of alkenes with hydrosilanes under mild conditions and low catalyst loadings.</description><subject>Alkenes</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical reactions</subject><subject>Chemical Sciences</subject><subject>Chemistry</subject><subject>Chemistry, Multidisciplinary</subject><subject>Crystallography</subject><subject>Inorganic chemistry</subject><subject>Mathematical analysis</subject><subject>Nickel</subject><subject>or physical chemistry</subject><subject>Phosphines</subject><subject>Physical Sciences</subject><subject>Science & Technology</subject><subject>Theoretical and</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>AOWDO</sourceid><sourceid>3HK</sourceid><recordid>eNqNkk1vEzEQhlcIRKvQC3dgKy4JaIs_1vbuBakKhSKigkQ5W16vl3Xj2KntTZXfwp_FSdpAe0D4YmvmmXdG4zfLnkNwAgGu37UgSADqms0fZYcIlLCgBNeP928EDrKjEK5AOhhDgtjT7ACXEKGawsPs11nXaamVjbkwc2VV3q9b74I2Impn8xsd-7zRYVwV14O2zqzNZNm7sOx1YscX3y4mudVyrkwuRRRmHWI4yS97lbduoa1Iut4ZlbsuT5prU7iV8tseunXFvcqoZa5tVH6hWi2iCs-yJ50wQR3d3qPsx8ezy-l5Mfv66fP0dFZIAlEs2qZsqVR1JxhkLSQlLJliZaOoFBUQlEIkCSOKtBDjBqaQULVqKcaiZKRjeJS93-kuhyb1lmkZXhi-9Hoh_Jo7ofn9jNU9_-lWvIKkRiVKApOdQP-g7Px0xjcxgChkELAVTOyrHSu9DlFbbp0XHIKKIF4RgMpEjG_H8e56UCHyhQ5SGSOsckPgiJSAIUDBZvLXD9ArN3iblsVRCUpKKEu_Psre3LV0IXjV7WeEgG9MxD-A79Otib4k-OXfy9ijd5ZJQLUDblTjurDxjlR7LLmMYEqrCqcXAlMdtz6ausHGVPr2_0sT_WJH-yD30B-7p_zxv_J82Xb4N3ZV-Ms</recordid><startdate>20200520</startdate><enddate>20200520</enddate><creator>Yang, Jian</creator><creator>Postils, Verònica</creator><creator>Lipschutz, Michael I</creator><creator>Fasulo, Meg</creator><creator>Raynaud, Christophe</creator><creator>Clot, Eric</creator><creator>Eisenstein, Odile</creator><creator>Tilley, T. Don</creator><general>Royal Soc Chemistry</general><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>1KM</scope><scope>AOWDO</scope><scope>BLEPL</scope><scope>DTL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>3HK</scope><scope>1XC</scope><scope>VOOES</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-8332-5545</orcidid><orcidid>https://orcid.org/0000-0003-0979-2051</orcidid><orcidid>https://orcid.org/0000-0002-6671-9099</orcidid><orcidid>https://orcid.org/0000-0002-7467-9277</orcidid><orcidid>https://orcid.org/0000-0001-5056-0311</orcidid><orcidid>https://orcid.org/0000-0002-9960-0633</orcidid></search><sort><creationdate>20200520</creationdate><title>Efficient alkene hydrosilation with bis(8-quinolyl)phosphine (NPN) nickel catalysts. The dominant role of silyl-over hydrido-nickel catalytic intermediates</title><author>Yang, Jian ; Postils, Verònica ; Lipschutz, Michael I ; Fasulo, Meg ; Raynaud, Christophe ; Clot, Eric ; Eisenstein, Odile ; Tilley, T. Don</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c512t-db4d6ce9fa717d154147e74be6ca80a6612c575e5d133b180aae9ed633a475f73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alkenes</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemical reactions</topic><topic>Chemical Sciences</topic><topic>Chemistry</topic><topic>Chemistry, Multidisciplinary</topic><topic>Crystallography</topic><topic>Inorganic chemistry</topic><topic>Mathematical analysis</topic><topic>Nickel</topic><topic>or physical chemistry</topic><topic>Phosphines</topic><topic>Physical Sciences</topic><topic>Science & Technology</topic><topic>Theoretical and</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yang, Jian</creatorcontrib><creatorcontrib>Postils, Verònica</creatorcontrib><creatorcontrib>Lipschutz, Michael I</creatorcontrib><creatorcontrib>Fasulo, Meg</creatorcontrib><creatorcontrib>Raynaud, Christophe</creatorcontrib><creatorcontrib>Clot, Eric</creatorcontrib><creatorcontrib>Eisenstein, Odile</creatorcontrib><creatorcontrib>Tilley, T. Don</creatorcontrib><collection>Index Chemicus</collection><collection>Web of Science - Science Citation Index Expanded - 2020</collection><collection>Web of Science Core Collection</collection><collection>Science Citation Index Expanded</collection><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>MEDLINE - Academic</collection><collection>NORA - Norwegian Open Research Archives</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yang, Jian</au><au>Postils, Verònica</au><au>Lipschutz, Michael I</au><au>Fasulo, Meg</au><au>Raynaud, Christophe</au><au>Clot, Eric</au><au>Eisenstein, Odile</au><au>Tilley, T. Don</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Efficient alkene hydrosilation with bis(8-quinolyl)phosphine (NPN) nickel catalysts. The dominant role of silyl-over hydrido-nickel catalytic intermediates</atitle><jtitle>Chemical science (Cambridge)</jtitle><stitle>CHEM SCI</stitle><addtitle>Chem Sci</addtitle><date>2020-05-20</date><risdate>2020</risdate><volume>11</volume><issue>19</issue><spage>543</spage><epage>551</epage><pages>543-551</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>A cationic nickel complex of the bis(8-quinolyl)(3,5-di-
tert
-butylphenoxy)phosphine (NPN) ligand, [(NPN)NiCl]
+
, is a precursor to efficient catalysts for the hydrosilation of alkenes with a variety of hydrosilanes under mild conditions and low catalyst loadings. DFT studies reveal the presence of two coupled catalytic cycles based on [(NPN)NiH]
+
and [(NPN)NiSiR
3
]
+
active species, with the latter being more efficient for producing the product. The preferred silyl-based catalysis is not due to a more facile insertion of alkene into the Ni-Si (
vs.
Ni-H) bond, but by consistent and efficient conversions of the hydride to the silyl complex.
A cationic nickel complex of the bis(8-quinolyl)(3,5-di-
tert
-butylphenoxy)phosphine (NPN) ligand, [(NPN)NiCl]
+
, is a precursor to efficient catalysts for the hydrosilation of alkenes with hydrosilanes under mild conditions and low catalyst loadings.</abstract><cop>CAMBRIDGE</cop><pub>Royal Soc Chemistry</pub><pmid>34122961</pmid><doi>10.1039/d0sc00997k</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0001-8332-5545</orcidid><orcidid>https://orcid.org/0000-0003-0979-2051</orcidid><orcidid>https://orcid.org/0000-0002-6671-9099</orcidid><orcidid>https://orcid.org/0000-0002-7467-9277</orcidid><orcidid>https://orcid.org/0000-0001-5056-0311</orcidid><orcidid>https://orcid.org/0000-0002-9960-0633</orcidid><oa>free_for_read</oa></addata></record> |
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| source | NORA - Norwegian Open Research Archives; DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central Open Access; PubMed Central |
| subjects | Alkenes Catalysis Catalysts Chemical reactions Chemical Sciences Chemistry Chemistry, Multidisciplinary Crystallography Inorganic chemistry Mathematical analysis Nickel or physical chemistry Phosphines Physical Sciences Science & Technology Theoretical and |
| title | Efficient alkene hydrosilation with bis(8-quinolyl)phosphine (NPN) nickel catalysts. The dominant role of silyl-over hydrido-nickel catalytic intermediates |
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