Ruthenium-catalyzed benzylic substitution of benzyl esters with stabilized carbon nucleophiles
We have accomplished the ruthenium-catalyzed benzylic substitution of benzyl esters with a stabilized carbon nucleophile. A [Cp*RuCl 2 ] 2 /picolinic acid catalyst system promoted the reaction of 2-naphthylmethyl-2,3,4,5,6-pentafluorobenzoates with a series of stabilized carbon nucleophiles such as...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2020-03, Vol.56 (22), p.3273-3276 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Suzuki, Koki Tsuji, Hiroaki Kawatsura, Motoi |
| description | We have accomplished the ruthenium-catalyzed benzylic substitution of benzyl esters with a stabilized carbon nucleophile. A [Cp*RuCl
2
]
2
/picolinic acid catalyst system promoted the reaction of 2-naphthylmethyl-2,3,4,5,6-pentafluorobenzoates with a series of stabilized carbon nucleophiles such as malonates, β-ketoesters, and diketones to give the corresponding benzylic alkylation products in moderate to high yields. We proposed a plausible reaction mechanism that could involve a (π-benzyl)ruthenium intermediate.
We have accomplished the ruthenium-catalyzed benzylic substitution of benzyl esters with a stabilized carbon nucleophile. |
| doi_str_mv | 10.1039/c9cc09899b |
| format | Article |
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2
]
2
/picolinic acid catalyst system promoted the reaction of 2-naphthylmethyl-2,3,4,5,6-pentafluorobenzoates with a series of stabilized carbon nucleophiles such as malonates, β-ketoesters, and diketones to give the corresponding benzylic alkylation products in moderate to high yields. We proposed a plausible reaction mechanism that could involve a (π-benzyl)ruthenium intermediate.
We have accomplished the ruthenium-catalyzed benzylic substitution of benzyl esters with a stabilized carbon nucleophile.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/c9cc09899b</identifier><identifier>PMID: 32073046</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alkylation ; Carbon ; Diketones ; Esters ; Nucleophiles ; Reaction mechanisms ; Ruthenium ; Substitution reactions</subject><ispartof>Chemical communications (Cambridge, England), 2020-03, Vol.56 (22), p.3273-3276</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c363t-146ee57f2443c8ba2e5799f00859bb90a5a68a334d3cf0294f1b552284ffee9a3</citedby><cites>FETCH-LOGICAL-c363t-146ee57f2443c8ba2e5799f00859bb90a5a68a334d3cf0294f1b552284ffee9a3</cites><orcidid>0000-0002-8899-3435 ; 0000-0002-8341-6866</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32073046$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Suzuki, Koki</creatorcontrib><creatorcontrib>Tsuji, Hiroaki</creatorcontrib><creatorcontrib>Kawatsura, Motoi</creatorcontrib><title>Ruthenium-catalyzed benzylic substitution of benzyl esters with stabilized carbon nucleophiles</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>We have accomplished the ruthenium-catalyzed benzylic substitution of benzyl esters with a stabilized carbon nucleophile. A [Cp*RuCl
2
]
2
/picolinic acid catalyst system promoted the reaction of 2-naphthylmethyl-2,3,4,5,6-pentafluorobenzoates with a series of stabilized carbon nucleophiles such as malonates, β-ketoesters, and diketones to give the corresponding benzylic alkylation products in moderate to high yields. We proposed a plausible reaction mechanism that could involve a (π-benzyl)ruthenium intermediate.
We have accomplished the ruthenium-catalyzed benzylic substitution of benzyl esters with a stabilized carbon nucleophile.</description><subject>Alkylation</subject><subject>Carbon</subject><subject>Diketones</subject><subject>Esters</subject><subject>Nucleophiles</subject><subject>Reaction mechanisms</subject><subject>Ruthenium</subject><subject>Substitution reactions</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp90c9LHDEUB_AgFX-1F--WKV5EmDaZl8wkRztoFRYEacGTQ5JJ2MjszDY_KLt_vdnuVqEHc0nC--Tx-AahU4K_EgzimxZaY8GFUHvoiEBNS0b544fNmYmyAcoO0XEIzzgvwvgBOoQKN4BpfYSeHlKcm9GlRalllMNqbfpCmXG9GpwuQlIhupiim8ZisrtCYUI0PhR_XJwXIUrlBrd5pqVX2Y1JD2Zazt1gwke0b-UQzKfdfoJ-3Vz_bG_L2f2Pu_ZqVmqoIZaE1sawxlaUguZKVvkihMWYM6GUwJLJmksA2oO2uBLUEsVYVXFqrTFCwgm62PZd-ul3yvN1Cxe0GQY5mimFrgLGWQOEQKbn_9HnKfkxT5dV09S8AiBZXW6V9lMI3thu6d1C-lVHcLdJvWtF2_5N_XvGn3ctk1qY_pX-izmDL1vgg36tvn1bt-xtNmfvGXgBVzWTYw</recordid><startdate>20200318</startdate><enddate>20200318</enddate><creator>Suzuki, Koki</creator><creator>Tsuji, Hiroaki</creator><creator>Kawatsura, Motoi</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-8899-3435</orcidid><orcidid>https://orcid.org/0000-0002-8341-6866</orcidid></search><sort><creationdate>20200318</creationdate><title>Ruthenium-catalyzed benzylic substitution of benzyl esters with stabilized carbon nucleophiles</title><author>Suzuki, Koki ; Tsuji, Hiroaki ; Kawatsura, Motoi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c363t-146ee57f2443c8ba2e5799f00859bb90a5a68a334d3cf0294f1b552284ffee9a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alkylation</topic><topic>Carbon</topic><topic>Diketones</topic><topic>Esters</topic><topic>Nucleophiles</topic><topic>Reaction mechanisms</topic><topic>Ruthenium</topic><topic>Substitution reactions</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Suzuki, Koki</creatorcontrib><creatorcontrib>Tsuji, Hiroaki</creatorcontrib><creatorcontrib>Kawatsura, Motoi</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Suzuki, Koki</au><au>Tsuji, Hiroaki</au><au>Kawatsura, Motoi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ruthenium-catalyzed benzylic substitution of benzyl esters with stabilized carbon nucleophiles</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2020-03-18</date><risdate>2020</risdate><volume>56</volume><issue>22</issue><spage>3273</spage><epage>3276</epage><pages>3273-3276</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>We have accomplished the ruthenium-catalyzed benzylic substitution of benzyl esters with a stabilized carbon nucleophile. A [Cp*RuCl
2
]
2
/picolinic acid catalyst system promoted the reaction of 2-naphthylmethyl-2,3,4,5,6-pentafluorobenzoates with a series of stabilized carbon nucleophiles such as malonates, β-ketoesters, and diketones to give the corresponding benzylic alkylation products in moderate to high yields. We proposed a plausible reaction mechanism that could involve a (π-benzyl)ruthenium intermediate.
We have accomplished the ruthenium-catalyzed benzylic substitution of benzyl esters with a stabilized carbon nucleophile.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>32073046</pmid><doi>10.1039/c9cc09899b</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-8899-3435</orcidid><orcidid>https://orcid.org/0000-0002-8341-6866</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2020-03, Vol.56 (22), p.3273-3276 |
| issn | 1359-7345 1364-548X |
| language | eng |
| recordid | cdi_proquest_journals_2377682331 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Alkylation Carbon Diketones Esters Nucleophiles Reaction mechanisms Ruthenium Substitution reactions |
| title | Ruthenium-catalyzed benzylic substitution of benzyl esters with stabilized carbon nucleophiles |
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