Solar Photochemical Oxidation of Alcohols using Catalytic Hydroquinone and Copper Nanoparticles under Oxygen: Oxidative Cleavage of Lignin Models
Alcohols are converted into to their corresponding carbonyl compounds using catalytic amounts of 1,4-hydroquinone with a copper nanoparticle electron transfer mediator with oxygen as the terminal oxidant in acetone as solvent under visible light irradiation. These conditions employing biorenewable h...
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| Veröffentlicht in: | Journal of organic chemistry 2014-11, Vol.79 (22), p.11091-11100 |
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| container_end_page | 11100 |
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| container_issue | 22 |
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| container_title | Journal of organic chemistry |
| container_volume | 79 |
| creator | Mitchell, Lorna J Moody, Christopher J |
| description | Alcohols are converted into to their corresponding carbonyl compounds using catalytic amounts of 1,4-hydroquinone with a copper nanoparticle electron transfer mediator with oxygen as the terminal oxidant in acetone as solvent under visible light irradiation. These conditions employing biorenewable hydroquinone as reagent were developed from initial experiments using stoichiometric amounts of 1,4-benzoquinone as oxidant. A range of benzylic and aliphatic primary and secondary alcohols are oxidized, affording the corresponding aldehydes or ketones in moderate to excellent yields. The methodology is also applicable to the oxidative degradation of lignin model compounds that undergo C–C bond cleavage to give simple aromatic compounds. |
| doi_str_mv | 10.1021/jo5020917 |
| format | Article |
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These conditions employing biorenewable hydroquinone as reagent were developed from initial experiments using stoichiometric amounts of 1,4-benzoquinone as oxidant. A range of benzylic and aliphatic primary and secondary alcohols are oxidized, affording the corresponding aldehydes or ketones in moderate to excellent yields. The methodology is also applicable to the oxidative degradation of lignin model compounds that undergo C–C bond cleavage to give simple aromatic compounds.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo5020917</identifier><identifier>PMID: 25322456</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alcohols - chemistry ; Catalysis ; Copper - chemistry ; Hydroquinones - chemistry ; Lignin - chemistry ; Nanoparticles - chemistry ; Oxidation-Reduction ; Oxygen - chemistry ; Photochemical Processes</subject><ispartof>Journal of organic chemistry, 2014-11, Vol.79 (22), p.11091-11100</ispartof><rights>Copyright © 2014 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-9eae73e595b0855024e8581fbf4f4eeb05238cbc59d0fd39c00fb4293d1788d63</citedby><cites>FETCH-LOGICAL-a381t-9eae73e595b0855024e8581fbf4f4eeb05238cbc59d0fd39c00fb4293d1788d63</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/jo5020917$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo5020917$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25322456$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mitchell, Lorna J</creatorcontrib><creatorcontrib>Moody, Christopher J</creatorcontrib><title>Solar Photochemical Oxidation of Alcohols using Catalytic Hydroquinone and Copper Nanoparticles under Oxygen: Oxidative Cleavage of Lignin Models</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Alcohols are converted into to their corresponding carbonyl compounds using catalytic amounts of 1,4-hydroquinone with a copper nanoparticle electron transfer mediator with oxygen as the terminal oxidant in acetone as solvent under visible light irradiation. These conditions employing biorenewable hydroquinone as reagent were developed from initial experiments using stoichiometric amounts of 1,4-benzoquinone as oxidant. A range of benzylic and aliphatic primary and secondary alcohols are oxidized, affording the corresponding aldehydes or ketones in moderate to excellent yields. The methodology is also applicable to the oxidative degradation of lignin model compounds that undergo C–C bond cleavage to give simple aromatic compounds.</description><subject>Alcohols - chemistry</subject><subject>Catalysis</subject><subject>Copper - chemistry</subject><subject>Hydroquinones - chemistry</subject><subject>Lignin - chemistry</subject><subject>Nanoparticles - chemistry</subject><subject>Oxidation-Reduction</subject><subject>Oxygen - chemistry</subject><subject>Photochemical Processes</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc9u1DAQxi0EokvhwAsgX5DKITC24_zhVkXQIi0sEnCOHHuy68prBzupuo_BG9erbXtiLiONft83-mYIecvgIwPOPt0ECRxaVj8jKyY5FFUL5XOyAuC8ELwSZ-RVSjeQS0r5kpxxKTgvZbUi_34FpyL9uQtz0DvcW60c3dxZo2YbPA0jvXQ67IJLdEnWb2mnZuUOs9X0-mBi-LtYHzxS5Q3twjRhpD-UD5OKGXGYVd7k2ebusEX_-dH5FmnnUN2qLR5XrO3WW0-_B4MuvSYvRuUSvnno5-TP1y-_u-tivbn61l2uCyUaNhctKqwFylYO0Micv8RGNmwcxnIsEQeQXDR60LI1MBrRaoBxKHkrDKubxlTinFycfKdjCkxzv7dJo3PKY1hSzypeQ90CNBn9cEJ1DClFHPsp2r2Kh55Bf_xA__SBzL57sF2GPZon8vHkGXh_ApROWbdEn1P-x-geYZyOlA</recordid><startdate>20141121</startdate><enddate>20141121</enddate><creator>Mitchell, Lorna J</creator><creator>Moody, Christopher J</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20141121</creationdate><title>Solar Photochemical Oxidation of Alcohols using Catalytic Hydroquinone and Copper Nanoparticles under Oxygen: Oxidative Cleavage of Lignin Models</title><author>Mitchell, Lorna J ; Moody, Christopher J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-9eae73e595b0855024e8581fbf4f4eeb05238cbc59d0fd39c00fb4293d1788d63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Alcohols - chemistry</topic><topic>Catalysis</topic><topic>Copper - chemistry</topic><topic>Hydroquinones - chemistry</topic><topic>Lignin - chemistry</topic><topic>Nanoparticles - chemistry</topic><topic>Oxidation-Reduction</topic><topic>Oxygen - chemistry</topic><topic>Photochemical Processes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mitchell, Lorna J</creatorcontrib><creatorcontrib>Moody, Christopher J</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</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>Mitchell, Lorna J</au><au>Moody, Christopher J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Solar Photochemical Oxidation of Alcohols using Catalytic Hydroquinone and Copper Nanoparticles under Oxygen: Oxidative Cleavage of Lignin Models</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2014-11-21</date><risdate>2014</risdate><volume>79</volume><issue>22</issue><spage>11091</spage><epage>11100</epage><pages>11091-11100</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Alcohols are converted into to their corresponding carbonyl compounds using catalytic amounts of 1,4-hydroquinone with a copper nanoparticle electron transfer mediator with oxygen as the terminal oxidant in acetone as solvent under visible light irradiation. These conditions employing biorenewable hydroquinone as reagent were developed from initial experiments using stoichiometric amounts of 1,4-benzoquinone as oxidant. A range of benzylic and aliphatic primary and secondary alcohols are oxidized, affording the corresponding aldehydes or ketones in moderate to excellent yields. The methodology is also applicable to the oxidative degradation of lignin model compounds that undergo C–C bond cleavage to give simple aromatic compounds.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>25322456</pmid><doi>10.1021/jo5020917</doi><tpages>10</tpages></addata></record> |
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| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2014-11, Vol.79 (22), p.11091-11100 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Alcohols - chemistry Catalysis Copper - chemistry Hydroquinones - chemistry Lignin - chemistry Nanoparticles - chemistry Oxidation-Reduction Oxygen - chemistry Photochemical Processes |
| title | Solar Photochemical Oxidation of Alcohols using Catalytic Hydroquinone and Copper Nanoparticles under Oxygen: Oxidative Cleavage of Lignin Models |
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