Double Ligands Enabled Ruthenium Catalyzed ortho‐C−H Arylation of Dialkyl Biarylphosphines: Straight and Economic Synthesis of Highly Steric and Electron‐Rich Aryl‐Substituted Buchwald‐Type Phosphines
A double‐ligands enabled ruthenium catalyzed C(sp2)−H arylation of dialkyl phosphines is described, which provides a straight access to aryl‐substituted dialkyl phosphine ligands. The combination of 1,3‐diketone and amino acid ligands is essential for this transformation. An important six‐membered c...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2021-06, Vol.363 (11), p.2843-2849 |
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| container_issue | 11 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Wang, Liang‐Neng Tang, Pan‐Ting Li, Ming Li, Jia‐Wei Liu, Yue‐Jin Zeng, Ming‐Hua |
| description | A double‐ligands enabled ruthenium catalyzed C(sp2)−H arylation of dialkyl phosphines is described, which provides a straight access to aryl‐substituted dialkyl phosphine ligands. The combination of 1,3‐diketone and amino acid ligands is essential for this transformation. An important six‐membered cycloruthenium intermediate was successfully isolated and characterized by X‐ray diffraction. Mechanistic studies showed that the 1,3‐diketone promoted the process of oxidative addition of cycloruthenium intermediate. Some of modified CyJohnPhos ligands exhibited highly catalytic activity in palladium catalyzed C−N bond formation. |
| doi_str_mv | 10.1002/adsc.202100283 |
| format | Article |
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The combination of 1,3‐diketone and amino acid ligands is essential for this transformation. An important six‐membered cycloruthenium intermediate was successfully isolated and characterized by X‐ray diffraction. Mechanistic studies showed that the 1,3‐diketone promoted the process of oxidative addition of cycloruthenium intermediate. Some of modified CyJohnPhos ligands exhibited highly catalytic activity in palladium catalyzed C−N bond formation.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.202100283</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Amino acids ; Aromatic compounds ; Catalytic activity ; C−H arylation ; Diketones ; double ligands ; Ligands ; Palladium ; Phosphines ; Ruthenium ; ruthenium catalysis ; Substitutes ; tertiary phosphines</subject><ispartof>Advanced synthesis & catalysis, 2021-06, Vol.363 (11), p.2843-2849</ispartof><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4203-b4e234964bf424b04f89fd913e31ca7ace508239402e37e75ca5b7d7df8315143</citedby><cites>FETCH-LOGICAL-c4203-b4e234964bf424b04f89fd913e31ca7ace508239402e37e75ca5b7d7df8315143</cites><orcidid>0000-0003-4226-0890</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%2Fadsc.202100283$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.202100283$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Wang, Liang‐Neng</creatorcontrib><creatorcontrib>Tang, Pan‐Ting</creatorcontrib><creatorcontrib>Li, Ming</creatorcontrib><creatorcontrib>Li, Jia‐Wei</creatorcontrib><creatorcontrib>Liu, Yue‐Jin</creatorcontrib><creatorcontrib>Zeng, Ming‐Hua</creatorcontrib><title>Double Ligands Enabled Ruthenium Catalyzed ortho‐C−H Arylation of Dialkyl Biarylphosphines: Straight and Economic Synthesis of Highly Steric and Electron‐Rich Aryl‐Substituted Buchwald‐Type Phosphines</title><title>Advanced synthesis & catalysis</title><description>A double‐ligands enabled ruthenium catalyzed C(sp2)−H arylation of dialkyl phosphines is described, which provides a straight access to aryl‐substituted dialkyl phosphine ligands. The combination of 1,3‐diketone and amino acid ligands is essential for this transformation. An important six‐membered cycloruthenium intermediate was successfully isolated and characterized by X‐ray diffraction. Mechanistic studies showed that the 1,3‐diketone promoted the process of oxidative addition of cycloruthenium intermediate. Some of modified CyJohnPhos ligands exhibited highly catalytic activity in palladium catalyzed C−N bond formation.</description><subject>Amino acids</subject><subject>Aromatic compounds</subject><subject>Catalytic activity</subject><subject>C−H arylation</subject><subject>Diketones</subject><subject>double ligands</subject><subject>Ligands</subject><subject>Palladium</subject><subject>Phosphines</subject><subject>Ruthenium</subject><subject>ruthenium catalysis</subject><subject>Substitutes</subject><subject>tertiary phosphines</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFUU1P2zAYjqZNGmO77mxp5xZ_pUm4lbTQSZU2UXaOHMchBtfObEconDhyRPw0fgK_ZG_p1B3ni9-P58PykyRfCZ4SjOmJaIKcUkx3Tc7eJUdkRtIJJ7Pi_aFO8cfkUwg3GJMsz7Kj5GXhhtootNbXwjYBLa2AtkGXQ-yU1cMWlSIKM97DzPnYudeHp_L18XmF5n40ImpnkWvRQgtzOxp0pgWM-86FvtNWhVO0iV7o6y4ikEdL6azbaok2owX9oMOOvIK9GQGpPKzecEbJ6J0Fs0stuzcvqDdDHaKOQ4THnA2yuxOmgfHV2Cv08-D5OfnQChPUl7_3cfLrfHlVribrHxffy_l6IjnFbFJzRRkvZrxuOeU15m1etE1BmGJEikxIleKcsoJjqlimslSKtM6arGlzRlLC2XHyba_be_d7UCFWN27wFiwrmrKcw2E5oKZ7lPQuBK_aqvd6C79UEVztoqp2uVWH3IBQ7Al32qjxP-hqvtiU_7h_AHtopXk</recordid><startdate>20210608</startdate><enddate>20210608</enddate><creator>Wang, Liang‐Neng</creator><creator>Tang, Pan‐Ting</creator><creator>Li, Ming</creator><creator>Li, Jia‐Wei</creator><creator>Liu, Yue‐Jin</creator><creator>Zeng, Ming‐Hua</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0003-4226-0890</orcidid></search><sort><creationdate>20210608</creationdate><title>Double Ligands Enabled Ruthenium Catalyzed ortho‐C−H Arylation of Dialkyl Biarylphosphines: Straight and Economic Synthesis of Highly Steric and Electron‐Rich Aryl‐Substituted Buchwald‐Type Phosphines</title><author>Wang, Liang‐Neng ; Tang, Pan‐Ting ; Li, Ming ; Li, Jia‐Wei ; Liu, Yue‐Jin ; Zeng, Ming‐Hua</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4203-b4e234964bf424b04f89fd913e31ca7ace508239402e37e75ca5b7d7df8315143</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Amino acids</topic><topic>Aromatic compounds</topic><topic>Catalytic activity</topic><topic>C−H arylation</topic><topic>Diketones</topic><topic>double ligands</topic><topic>Ligands</topic><topic>Palladium</topic><topic>Phosphines</topic><topic>Ruthenium</topic><topic>ruthenium catalysis</topic><topic>Substitutes</topic><topic>tertiary phosphines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Liang‐Neng</creatorcontrib><creatorcontrib>Tang, Pan‐Ting</creatorcontrib><creatorcontrib>Li, Ming</creatorcontrib><creatorcontrib>Li, Jia‐Wei</creatorcontrib><creatorcontrib>Liu, Yue‐Jin</creatorcontrib><creatorcontrib>Zeng, Ming‐Hua</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Liang‐Neng</au><au>Tang, Pan‐Ting</au><au>Li, Ming</au><au>Li, Jia‐Wei</au><au>Liu, Yue‐Jin</au><au>Zeng, Ming‐Hua</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Double Ligands Enabled Ruthenium Catalyzed ortho‐C−H Arylation of Dialkyl Biarylphosphines: Straight and Economic Synthesis of Highly Steric and Electron‐Rich Aryl‐Substituted Buchwald‐Type Phosphines</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2021-06-08</date><risdate>2021</risdate><volume>363</volume><issue>11</issue><spage>2843</spage><epage>2849</epage><pages>2843-2849</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A double‐ligands enabled ruthenium catalyzed C(sp2)−H arylation of dialkyl phosphines is described, which provides a straight access to aryl‐substituted dialkyl phosphine ligands. 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| subjects | Amino acids Aromatic compounds Catalytic activity C−H arylation Diketones double ligands Ligands Palladium Phosphines Ruthenium ruthenium catalysis Substitutes tertiary phosphines |
| title | Double Ligands Enabled Ruthenium Catalyzed ortho‐C−H Arylation of Dialkyl Biarylphosphines: Straight and Economic Synthesis of Highly Steric and Electron‐Rich Aryl‐Substituted Buchwald‐Type Phosphines |
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