Aluminium-catalysed synthesis of aryl enol ethers from phenols and dimethyl ketals
We report an environmentally friendly, aluminium-catalysed, halide- and transition metal-free method for the synthesis of aryl enol ethers from phenols and dimethyl ketals that involves ketal exchange driven by the removal of methanol. The obtained aryl enol ethers were transformed into the correspo...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2023-10, Vol.21 (41), p.8259-8262 |
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| container_issue | 41 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Kobayashi, Kwihwan Komatsuzaki, Shingo Onozawa, Shun-ya Masuda, Koichiro Kobayashi, Sh |
| description | We report an environmentally friendly, aluminium-catalysed, halide- and transition metal-free method for the synthesis of aryl enol ethers from phenols and dimethyl ketals that involves ketal exchange driven by the removal of methanol. The obtained aryl enol ethers were transformed into the corresponding diaryl ethers by Pd/C-catalysed dehydrogenation or DDQ oxidation.
We have developed a new halide- and transition metal-free protocol for the synthesis of aryl enol ethers from phenols and dimethyl ketals, which are important intermediates or building blocks in organic synthesis and polymer chemistry. |
| doi_str_mv | 10.1039/d3ob01266b |
| format | Article |
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We have developed a new halide- and transition metal-free protocol for the synthesis of aryl enol ethers from phenols and dimethyl ketals, which are important intermediates or building blocks in organic synthesis and polymer chemistry.</description><subject>Aluminum</subject><subject>Aromatic compounds</subject><subject>Chemical synthesis</subject><subject>Dehydrogenation</subject><subject>Diaryl ethers</subject><subject>Ethers</subject><subject>Oxidation</subject><subject>Palladium</subject><subject>Phenols</subject><subject>Transition metals</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpd0M9LwzAUB_AgCs7pxbsQ8CJCNWl-tcdt_oTBQPRc0uSVdbbNTNpD_3szJxO85IWXD4-XL0KXlNxRwvJ7y1xJaCpleYQmlCuVEMHy48M9JafoLIQNITRXkk_Q26wZ2rqrhzYxutfNGMDiMHb9GkIdsKuw9mODoXPxiE0fcOVdi7frXStg3Vls6zY-RfUJcUI4RydVLHDxW6fo4-nxffGSLFfPr4vZMjGM8j5JUw7A8pKLkhllIdXaSsGqjAFYmguViUrSvFKWCmIIU0ITKEGB4SQ1mWJTdLOfu_Xua4DQF20dDDSN7sANoUgzyZRUQvFIr__RjRt8F7eLKqNUcsJoVLd7ZbwLwUNVbH3dxv8XlBS7eIsHtpr_xDuP-GqPfTAH9xc_-wa9ancC</recordid><startdate>20231025</startdate><enddate>20231025</enddate><creator>Kobayashi, Kwihwan</creator><creator>Komatsuzaki, Shingo</creator><creator>Onozawa, Shun-ya</creator><creator>Masuda, Koichiro</creator><creator>Kobayashi, Sh</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-8235-4368</orcidid><orcidid>https://orcid.org/0000-0002-5289-8348</orcidid><orcidid>https://orcid.org/0000-0002-9926-7308</orcidid></search><sort><creationdate>20231025</creationdate><title>Aluminium-catalysed synthesis of aryl enol ethers from phenols and dimethyl ketals</title><author>Kobayashi, Kwihwan ; Komatsuzaki, Shingo ; Onozawa, Shun-ya ; Masuda, Koichiro ; Kobayashi, Sh</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c314t-224ee39b45b3c7de2aad653f83eed195785f619f7d150c0375a0ebe7ec402c873</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Aluminum</topic><topic>Aromatic compounds</topic><topic>Chemical synthesis</topic><topic>Dehydrogenation</topic><topic>Diaryl ethers</topic><topic>Ethers</topic><topic>Oxidation</topic><topic>Palladium</topic><topic>Phenols</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kobayashi, Kwihwan</creatorcontrib><creatorcontrib>Komatsuzaki, Shingo</creatorcontrib><creatorcontrib>Onozawa, Shun-ya</creatorcontrib><creatorcontrib>Masuda, Koichiro</creatorcontrib><creatorcontrib>Kobayashi, Sh</creatorcontrib><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kobayashi, Kwihwan</au><au>Komatsuzaki, Shingo</au><au>Onozawa, Shun-ya</au><au>Masuda, Koichiro</au><au>Kobayashi, Sh</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Aluminium-catalysed synthesis of aryl enol ethers from phenols and dimethyl ketals</atitle><jtitle>Organic & biomolecular chemistry</jtitle><date>2023-10-25</date><risdate>2023</risdate><volume>21</volume><issue>41</issue><spage>8259</spage><epage>8262</epage><pages>8259-8262</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>We report an environmentally friendly, aluminium-catalysed, halide- and transition metal-free method for the synthesis of aryl enol ethers from phenols and dimethyl ketals that involves ketal exchange driven by the removal of methanol. The obtained aryl enol ethers were transformed into the corresponding diaryl ethers by Pd/C-catalysed dehydrogenation or DDQ oxidation.
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| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2023-10, Vol.21 (41), p.8259-8262 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_rsc_primary_d3ob01266b |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Aluminum Aromatic compounds Chemical synthesis Dehydrogenation Diaryl ethers Ethers Oxidation Palladium Phenols Transition metals |
| title | Aluminium-catalysed synthesis of aryl enol ethers from phenols and dimethyl ketals |
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