A Ruthenium−Dihydrogen Putative Intermediate in Ketone Hydrogenation
The compound fac-[Ru((R)-BINAP)(H)(2-PrOH)3]+ (6) (BINAP = 2,2‘-bis(diphenylphosphino)-1,1‘-binaphthyl) reacts with (R,R)-dpen (dpen = 1,2-diphenylethylenediamine) under H2 at −60 °C in 2-PrOH-d 8/CD2Cl2 to generate the cationic dihydrogen putative intermediate trans-[Ru((R)-BINAP)(H)(η2-H2)((R,R)-d...
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| Veröffentlicht in: | Journal of the American Chemical Society 2005-03, Vol.127 (12), p.4152-4153 |
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| container_end_page | 4153 |
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| container_issue | 12 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 127 |
| creator | Hamilton, Robin J Leong, Carolyn G Bigam, Glen Miskolzie, Mark Bergens, Steven H |
| description | The compound fac-[Ru((R)-BINAP)(H)(2-PrOH)3]+ (6) (BINAP = 2,2‘-bis(diphenylphosphino)-1,1‘-binaphthyl) reacts with (R,R)-dpen (dpen = 1,2-diphenylethylenediamine) under H2 at −60 °C in 2-PrOH-d 8/CD2Cl2 to generate the cationic dihydrogen putative intermediate trans-[Ru((R)-BINAP)(H)(η2-H2)((R,R)-dpen)]+ (2‘) without H−D exchange between the hydrogen ligands and the solvent. A 1H NMR study concludes that the dihydrogen ligand in 2‘ does not protonate 2-PrOH to a catalytically significant extent, and that 2‘ requires an added base or hydride source to be an active catalyst. |
| doi_str_mv | 10.1021/ja043339k |
| format | Article |
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A 1H NMR study concludes that the dihydrogen ligand in 2‘ does not protonate 2-PrOH to a catalytically significant extent, and that 2‘ requires an added base or hydride source to be an active catalyst.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja043339k</identifier><identifier>PMID: 15783180</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemical reactivity ; Chemistry ; Exact sciences and technology ; Organic chemistry ; Reactivity and mechanisms</subject><ispartof>Journal of the American Chemical Society, 2005-03, Vol.127 (12), p.4152-4153</ispartof><rights>Copyright © 2005 American Chemical Society</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-99d6f02df21d06b1e1ef49c1045fa297e5cf5818e8beaea5d279271abd5fe0fd3</citedby><cites>FETCH-LOGICAL-a381t-99d6f02df21d06b1e1ef49c1045fa297e5cf5818e8beaea5d279271abd5fe0fd3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ja043339k$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja043339k$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27065,27913,27914,56727,56777</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16634586$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15783180$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hamilton, Robin J</creatorcontrib><creatorcontrib>Leong, Carolyn G</creatorcontrib><creatorcontrib>Bigam, Glen</creatorcontrib><creatorcontrib>Miskolzie, Mark</creatorcontrib><creatorcontrib>Bergens, Steven H</creatorcontrib><title>A Ruthenium−Dihydrogen Putative Intermediate in Ketone Hydrogenation</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>The compound fac-[Ru((R)-BINAP)(H)(2-PrOH)3]+ (6) (BINAP = 2,2‘-bis(diphenylphosphino)-1,1‘-binaphthyl) reacts with (R,R)-dpen (dpen = 1,2-diphenylethylenediamine) under H2 at −60 °C in 2-PrOH-d 8/CD2Cl2 to generate the cationic dihydrogen putative intermediate trans-[Ru((R)-BINAP)(H)(η2-H2)((R,R)-dpen)]+ (2‘) without H−D exchange between the hydrogen ligands and the solvent. A 1H NMR study concludes that the dihydrogen ligand in 2‘ does not protonate 2-PrOH to a catalytically significant extent, and that 2‘ requires an added base or hydride source to be an active catalyst.</description><subject>Chemical reactivity</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Organic chemistry</subject><subject>Reactivity and mechanisms</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNpt0MlOwzAQBmALgWgpHHgBlAtIHAJe4ixHtpaKCiqWs-UmY3BpnWI7CN6AM4_Ik2DUqL1wskb-9GvmR2if4BOCKTmdSpwwxorXDdQlnOKYE5puoi7GmMZZnrIO2nFuGsaE5mQbdQjPckZy3EX9s-i-8S9gdDP_-fq-1C-fla2fwUTjxkuv3yEaGg92DpWWHiJtohvwtYHouoUB1WYXbSk5c7DXvj301L96vLiOR3eD4cXZKJYsJz4uiipVmFaKkgqnEwIEVFKUBCdcSVpkwEvFc5JDPgEJklc0K2hG5KTiCrCqWA8dLXMXtn5rwHkx166E2UwaqBsn0ownDFMe4PESlrZ2zoISC6vn0n4KgsVfaWJVWrAHbWgzCXeuZdtSAIctkK6UM2WlKbVbuzRlCQ8191C8dNp5-Fj9S_saFmMZF4_jB3HbP8eD83EiLte5snRiWjfWhO7-WfAX4UGQng</recordid><startdate>20050330</startdate><enddate>20050330</enddate><creator>Hamilton, Robin J</creator><creator>Leong, Carolyn G</creator><creator>Bigam, Glen</creator><creator>Miskolzie, Mark</creator><creator>Bergens, Steven H</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20050330</creationdate><title>A Ruthenium−Dihydrogen Putative Intermediate in Ketone Hydrogenation</title><author>Hamilton, Robin J ; Leong, Carolyn G ; Bigam, Glen ; Miskolzie, Mark ; Bergens, Steven H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-99d6f02df21d06b1e1ef49c1045fa297e5cf5818e8beaea5d279271abd5fe0fd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Chemical reactivity</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Organic chemistry</topic><topic>Reactivity and mechanisms</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hamilton, Robin J</creatorcontrib><creatorcontrib>Leong, Carolyn G</creatorcontrib><creatorcontrib>Bigam, Glen</creatorcontrib><creatorcontrib>Miskolzie, Mark</creatorcontrib><creatorcontrib>Bergens, Steven H</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hamilton, Robin J</au><au>Leong, Carolyn G</au><au>Bigam, Glen</au><au>Miskolzie, Mark</au><au>Bergens, Steven H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Ruthenium−Dihydrogen Putative Intermediate in Ketone Hydrogenation</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2005-03-30</date><risdate>2005</risdate><volume>127</volume><issue>12</issue><spage>4152</spage><epage>4153</epage><pages>4152-4153</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>The compound fac-[Ru((R)-BINAP)(H)(2-PrOH)3]+ (6) (BINAP = 2,2‘-bis(diphenylphosphino)-1,1‘-binaphthyl) reacts with (R,R)-dpen (dpen = 1,2-diphenylethylenediamine) under H2 at −60 °C in 2-PrOH-d 8/CD2Cl2 to generate the cationic dihydrogen putative intermediate trans-[Ru((R)-BINAP)(H)(η2-H2)((R,R)-dpen)]+ (2‘) without H−D exchange between the hydrogen ligands and the solvent. A 1H NMR study concludes that the dihydrogen ligand in 2‘ does not protonate 2-PrOH to a catalytically significant extent, and that 2‘ requires an added base or hydride source to be an active catalyst.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15783180</pmid><doi>10.1021/ja043339k</doi><tpages>2</tpages></addata></record> |
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| subjects | Chemical reactivity Chemistry Exact sciences and technology Organic chemistry Reactivity and mechanisms |
| title | A Ruthenium−Dihydrogen Putative Intermediate in Ketone Hydrogenation |
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