Synthesis of Cyclobutene‐Fused Eight‐Membered Carbocycles through Gold‐Catalyzed Intramolecular Enyne [2+2] Cycloaddition
Cationic gold(I) complexes with hollow‐shaped triethynylphosphine ligands efficiently catalyzed intramolecular [2+2] cycloaddition of 1,9‐enynes to afford cyclobutene‐fused eight‐membered carbocycles that were difficult to synthesize by other catalytic systems. Various 1,9‐enynes with carbon linkers...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2018-02, Vol.360 (4), p.670-675 |
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| creator | Iwai, Tomohiro Ueno, Masahiro Okochi, Hiori Sawamura, Masaya |
| description | Cationic gold(I) complexes with hollow‐shaped triethynylphosphine ligands efficiently catalyzed intramolecular [2+2] cycloaddition of 1,9‐enynes to afford cyclobutene‐fused eight‐membered carbocycles that were difficult to synthesize by other catalytic systems. Various 1,9‐enynes with carbon linkers with or without a fused ring underwent efficient [2+2] cycloaddition with 5 mol% of the Au catalyst bearing the triarylmethyl‐end‐capped triethynylphosphine in CH2Cl2 at rt in the presence of MS 4A as an additive. More challenging 1,9‐enyne substrates with fully saturated acyclic carbon linkers underwent eight‐membered ring formation at 60 °C in ClCH2CH2Cl in the absence of MS 4A, forming monocyclic 1,3‐dienes as major products. |
| doi_str_mv | 10.1002/adsc.201701193 |
| format | Article |
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Various 1,9‐enynes with carbon linkers with or without a fused ring underwent efficient [2+2] cycloaddition with 5 mol% of the Au catalyst bearing the triarylmethyl‐end‐capped triethynylphosphine in CH2Cl2 at rt in the presence of MS 4A as an additive. More challenging 1,9‐enyne substrates with fully saturated acyclic carbon linkers underwent eight‐membered ring formation at 60 °C in ClCH2CH2Cl in the absence of MS 4A, forming monocyclic 1,3‐dienes as major products.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201701193</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Catalysis ; Chemical synthesis ; Coordination compounds ; Cycloaddition ; cyclobutene ; cycloisomerization ; Dienes ; enyne ; Gold ; medium-ring compounds ; Substrates</subject><ispartof>Advanced synthesis & catalysis, 2018-02, Vol.360 (4), p.670-675</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. 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More challenging 1,9‐enyne substrates with fully saturated acyclic carbon linkers underwent eight‐membered ring formation at 60 °C in ClCH2CH2Cl in the absence of MS 4A, forming monocyclic 1,3‐dienes as major products.</description><subject>Catalysis</subject><subject>Chemical synthesis</subject><subject>Coordination compounds</subject><subject>Cycloaddition</subject><subject>cyclobutene</subject><subject>cycloisomerization</subject><subject>Dienes</subject><subject>enyne</subject><subject>Gold</subject><subject>medium-ring compounds</subject><subject>Substrates</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkMtKw0AUhoMoWKtb1wGXkjqXtOksS2xroeKiuhIJJzMnTUqaqTMJEjf6CD6jT-KUSF26Ohe-_xz4PO-SkgElhN2AsnLACI0IpYIfeT06osMgpCNxfOiH5NQ7s3ZDHDaOop73sWqrOkdbWF9nftzKUqdNjRV-f37NGovKnxbrvHbTPW5TNG4Rg0m1dCRav86Nbta5P9elckwMNZTtu4MWVW1gq0uUTQnGn1Zthf4zu2Yv3RNQqqgLXZ17JxmUFi9-a997mk0f47tg-TBfxJNlIENGeCBUiFyM-QiFSpkkgCKVEDFUhGV8TFFkJAUVhYwzKWAImCrKOQIjEiiEvO9ddXd3Rr82aOtkoxtTuZcJc_Io5c6IowYdJY221mCW7EyxBdMmlCR7yclecnKQ7AKiC7wVJbb_0MnkdhX_ZX8AXUCF_Q</recordid><startdate>20180215</startdate><enddate>20180215</enddate><creator>Iwai, Tomohiro</creator><creator>Ueno, Masahiro</creator><creator>Okochi, Hiori</creator><creator>Sawamura, Masaya</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20180215</creationdate><title>Synthesis of Cyclobutene‐Fused Eight‐Membered Carbocycles through Gold‐Catalyzed Intramolecular Enyne [2+2] Cycloaddition</title><author>Iwai, Tomohiro ; Ueno, Masahiro ; Okochi, Hiori ; Sawamura, Masaya</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4203-9d4e39836e9db2c0ae9bca72ed02f381e9f0bad74232c9a5aebd133ea20ca1a43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Catalysis</topic><topic>Chemical synthesis</topic><topic>Coordination compounds</topic><topic>Cycloaddition</topic><topic>cyclobutene</topic><topic>cycloisomerization</topic><topic>Dienes</topic><topic>enyne</topic><topic>Gold</topic><topic>medium-ring compounds</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Iwai, Tomohiro</creatorcontrib><creatorcontrib>Ueno, Masahiro</creatorcontrib><creatorcontrib>Okochi, Hiori</creatorcontrib><creatorcontrib>Sawamura, Masaya</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Iwai, Tomohiro</au><au>Ueno, Masahiro</au><au>Okochi, Hiori</au><au>Sawamura, Masaya</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Cyclobutene‐Fused Eight‐Membered Carbocycles through Gold‐Catalyzed Intramolecular Enyne [2+2] Cycloaddition</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2018-02-15</date><risdate>2018</risdate><volume>360</volume><issue>4</issue><spage>670</spage><epage>675</epage><pages>670-675</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>Cationic gold(I) complexes with hollow‐shaped triethynylphosphine ligands efficiently catalyzed intramolecular [2+2] cycloaddition of 1,9‐enynes to afford cyclobutene‐fused eight‐membered carbocycles that were difficult to synthesize by other catalytic systems. Various 1,9‐enynes with carbon linkers with or without a fused ring underwent efficient [2+2] cycloaddition with 5 mol% of the Au catalyst bearing the triarylmethyl‐end‐capped triethynylphosphine in CH2Cl2 at rt in the presence of MS 4A as an additive. More challenging 1,9‐enyne substrates with fully saturated acyclic carbon linkers underwent eight‐membered ring formation at 60 °C in ClCH2CH2Cl in the absence of MS 4A, forming monocyclic 1,3‐dienes as major products.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.201701193</doi><tpages>6</tpages></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Catalysis Chemical synthesis Coordination compounds Cycloaddition cyclobutene cycloisomerization Dienes enyne Gold medium-ring compounds Substrates |
| title | Synthesis of Cyclobutene‐Fused Eight‐Membered Carbocycles through Gold‐Catalyzed Intramolecular Enyne [2+2] Cycloaddition |
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