A Triruthenium Carbonyl Cluster Bearing a Bridging Acenaphthylene Ligand: An Efficient Catalyst for Reduction of Esters, Carboxylic Acids, and Amides by Trialkylsilanes
An efficient reduction of carboxylic acids, esters, and amides with trialkylsilanes is accomplished using a triruthenium carbonyl cluster bearing a bridging acenaphthylene ligand, (μ3,η2:η3:η5-acenaphthylene)Ru3(CO)7, as the catalyst. Preactivation of the catalyst by hydrosilanes accelerates the rea...
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Veröffentlicht in: | Journal of organic chemistry 2002-07, Vol.67 (14), p.4985-4988 |
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container_title | Journal of organic chemistry |
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creator | Matsubara, Kouki Iura, Takafumi Maki, Tomoyuki Nagashima, Hideo |
description | An efficient reduction of carboxylic acids, esters, and amides with trialkylsilanes is accomplished using a triruthenium carbonyl cluster bearing a bridging acenaphthylene ligand, (μ3,η2:η3:η5-acenaphthylene)Ru3(CO)7, as the catalyst. Preactivation of the catalyst by hydrosilanes accelerates the reactions. Sterically small trialkylsilanes are effective in these reactions. Reduction of carboxylic acids and amides efficiently produces the corresponding silyl ethers and amines, respectively. Reduction of esters gives a mixture of silyl and alkyl ethers, but can be controlled by changing the silanes and solvents. |
doi_str_mv | 10.1021/jo025726n |
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Preactivation of the catalyst by hydrosilanes accelerates the reactions. Sterically small trialkylsilanes are effective in these reactions. Reduction of carboxylic acids and amides efficiently produces the corresponding silyl ethers and amines, respectively. 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Reduction of esters gives a mixture of silyl and alkyl ethers, but can be controlled by changing the silanes and solvents.</description><subject>Aliphatic compounds</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><recordid>eNptkc1u1DAURi0EokNhwQsgb0BCIuDY8c-wS6MpRZoKBMM6chx7xq3jDHYiNTu2fZa-FU-Coxl1Nnhj6_ro3E_3AvA6Rx9zhPNPNz3ClGPmn4BFTjHK2BIVT8ECIYwzghk5Ay9ivEHpUEqfg7Mco6UgGC3AQwk3wYZx2Glvxw5WMjS9nxys3BgHHeCFlsH6LZTwIth2Oz9Lpb3c74bd5LTXcG230ref__65h6WHK2OsstoPSTVIN8UBmj7AH7od1WB7D3sDV7M5fjg0u5ucVclp21RJIlh2ttURNtOcTLrbyUXrpNfxJXhmpIv61fE-B78uV5vqKlt_-_K1KteZLAo6ZLihS5IXiBa8QboVUhmhhRBMYsMaiRvCCpoKiOmGt4RraYRQohG05VyTgpyDdwfvPvS_Rx2HurNRaTeH6MdY81zwZF8m8P0BVKGPMWhT74PtZJjqHNXzZurHzST2zVE6Np1uT-RxFQl4ewRkVNKZIL2y8cQRzlmB56bZgbNpineP_zLc1owTTuvN95_11bXYXK_ZZV2dvFLFlGcMPs3uPwH_AbeBs_k</recordid><startdate>20020712</startdate><enddate>20020712</enddate><creator>Matsubara, Kouki</creator><creator>Iura, Takafumi</creator><creator>Maki, Tomoyuki</creator><creator>Nagashima, Hideo</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>20020712</creationdate><title>A Triruthenium Carbonyl Cluster Bearing a Bridging Acenaphthylene Ligand: An Efficient Catalyst for Reduction of Esters, Carboxylic Acids, and Amides by Trialkylsilanes</title><author>Matsubara, Kouki ; Iura, Takafumi ; Maki, Tomoyuki ; Nagashima, Hideo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-2b593140547b0ed8acf8e8886a2f6ba2b3645e8806eb7d37eaf88c8b85d77e343</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Aliphatic compounds</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Matsubara, Kouki</creatorcontrib><creatorcontrib>Iura, Takafumi</creatorcontrib><creatorcontrib>Maki, Tomoyuki</creatorcontrib><creatorcontrib>Nagashima, Hideo</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Matsubara, Kouki</au><au>Iura, Takafumi</au><au>Maki, Tomoyuki</au><au>Nagashima, Hideo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Triruthenium Carbonyl Cluster Bearing a Bridging Acenaphthylene Ligand: An Efficient Catalyst for Reduction of Esters, Carboxylic Acids, and Amides by Trialkylsilanes</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2002-07-12</date><risdate>2002</risdate><volume>67</volume><issue>14</issue><spage>4985</spage><epage>4988</epage><pages>4985-4988</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>An efficient reduction of carboxylic acids, esters, and amides with trialkylsilanes is accomplished using a triruthenium carbonyl cluster bearing a bridging acenaphthylene ligand, (μ3,η2:η3:η5-acenaphthylene)Ru3(CO)7, as the catalyst. Preactivation of the catalyst by hydrosilanes accelerates the reactions. Sterically small trialkylsilanes are effective in these reactions. Reduction of carboxylic acids and amides efficiently produces the corresponding silyl ethers and amines, respectively. Reduction of esters gives a mixture of silyl and alkyl ethers, but can be controlled by changing the silanes and solvents.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12098320</pmid><doi>10.1021/jo025726n</doi><tpages>4</tpages></addata></record> |
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source | ACS Publications |
subjects | Aliphatic compounds Chemistry Exact sciences and technology Organic chemistry Preparations and properties |
title | A Triruthenium Carbonyl Cluster Bearing a Bridging Acenaphthylene Ligand: An Efficient Catalyst for Reduction of Esters, Carboxylic Acids, and Amides by Trialkylsilanes |
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