Efficient Vanadium‐Catalyzed Aerobic C−C Bond Oxidative Cleavage of Vicinal Diols
The aerobic oxidative C−C bond cleavage of vicinal diols catalyzed by vanadium amino triphenolates is described. Our results show that C−C bond cleavage can be performed in different solvents, under an air or oxygen atmosphere, with a large variety of glycols (cyclic or linear, with aromatic or alip...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2018-09, Vol.360 (17), p.3286-3296 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Amadio, Emanuele González‐Fabra, Joan Carraro, Davide Denis, William Gjoka, Blerina Zonta, Cristiano Bartik, Kristin Cavani, Fabrizio Solmi, Stefania Bo, Carles Licini, Giulia |
| description | The aerobic oxidative C−C bond cleavage of vicinal diols catalyzed by vanadium amino triphenolates is described. Our results show that C−C bond cleavage can be performed in different solvents, under an air or oxygen atmosphere, with a large variety of glycols (cyclic or linear, with aromatic or aliphatic substituents) affording the corresponding carbonyl derivatives with high chemoselectivity. Reactions can be performed with as little as 10 ppm of catalyst reaching TON up to 81,000 and TOFs of up to 4150 h−1. A reaction mechanism, rationalized by density functional theory calculations, is also proposed. |
| doi_str_mv | 10.1002/adsc.201800050 |
| format | Article |
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Our results show that C−C bond cleavage can be performed in different solvents, under an air or oxygen atmosphere, with a large variety of glycols (cyclic or linear, with aromatic or aliphatic substituents) affording the corresponding carbonyl derivatives with high chemoselectivity. Reactions can be performed with as little as 10 ppm of catalyst reaching TON up to 81,000 and TOFs of up to 4150 h−1. 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Our results show that C−C bond cleavage can be performed in different solvents, under an air or oxygen atmosphere, with a large variety of glycols (cyclic or linear, with aromatic or aliphatic substituents) affording the corresponding carbonyl derivatives with high chemoselectivity. Reactions can be performed with as little as 10 ppm of catalyst reaching TON up to 81,000 and TOFs of up to 4150 h−1. A reaction mechanism, rationalized by density functional theory calculations, is also proposed.</description><subject>Aerobic Oxidation</subject><subject>Aliphatic compounds</subject><subject>Carbonyls</subject><subject>Cleavage</subject><subject>C−C Activation</subject><subject>Density functional theory</subject><subject>Diols</subject><subject>Homogeneous Catalysis</subject><subject>Oxygen</subject><subject>Reaction mechanisms</subject><subject>Vanadium</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkDtPAkEUhSdGExFtrSexBu_MPqfEBR8JCYVCu5nHHTNk2cWdBcXK0tL4E_klLsFgaXVP8X0nN4eQSwZ9BsCvpfG6z4GlABDBEemwmEW9kMXi-JAjOCVn3s8BWJImSYdMR9Y67bBs6EyW0rjVYvvxlclGFpt3NHSAdaWcptn28zujN1Vp6OTNGdm4NdKsQLmWz0grS2dtSykLOnRV4c_JiZWFx4vf2yXT29FTdt8bT-4essG4p8MYoGcDJZiwEAYp8AgDhQKjCBG4DHgKGq1KuOagmFZobIwmtJJFKBRTYHQQdMnVvndZVy8r9E0-r1Z1-4bPOYg0DpiIoKX6e0rXlfc12nxZu4WsNzmDfDddvpsuP0zXCmIvvLoCN__Q-WD4mP25P6IrdD8</recordid><startdate>20180903</startdate><enddate>20180903</enddate><creator>Amadio, Emanuele</creator><creator>González‐Fabra, Joan</creator><creator>Carraro, Davide</creator><creator>Denis, William</creator><creator>Gjoka, Blerina</creator><creator>Zonta, Cristiano</creator><creator>Bartik, Kristin</creator><creator>Cavani, Fabrizio</creator><creator>Solmi, Stefania</creator><creator>Bo, Carles</creator><creator>Licini, Giulia</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>20180903</creationdate><title>Efficient Vanadium‐Catalyzed Aerobic C−C Bond Oxidative Cleavage of Vicinal Diols</title><author>Amadio, Emanuele ; González‐Fabra, Joan ; Carraro, Davide ; Denis, William ; Gjoka, Blerina ; Zonta, Cristiano ; Bartik, Kristin ; Cavani, Fabrizio ; Solmi, Stefania ; Bo, Carles ; Licini, Giulia</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4600-f3b919f0438025e3be9e55ee02a3280cefb72c20b1cbedf6ed4fa15e9b1b0dc33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Aerobic Oxidation</topic><topic>Aliphatic compounds</topic><topic>Carbonyls</topic><topic>Cleavage</topic><topic>C−C Activation</topic><topic>Density functional theory</topic><topic>Diols</topic><topic>Homogeneous Catalysis</topic><topic>Oxygen</topic><topic>Reaction mechanisms</topic><topic>Vanadium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Amadio, Emanuele</creatorcontrib><creatorcontrib>González‐Fabra, Joan</creatorcontrib><creatorcontrib>Carraro, Davide</creatorcontrib><creatorcontrib>Denis, William</creatorcontrib><creatorcontrib>Gjoka, Blerina</creatorcontrib><creatorcontrib>Zonta, Cristiano</creatorcontrib><creatorcontrib>Bartik, Kristin</creatorcontrib><creatorcontrib>Cavani, Fabrizio</creatorcontrib><creatorcontrib>Solmi, Stefania</creatorcontrib><creatorcontrib>Bo, Carles</creatorcontrib><creatorcontrib>Licini, Giulia</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>Amadio, Emanuele</au><au>González‐Fabra, Joan</au><au>Carraro, Davide</au><au>Denis, William</au><au>Gjoka, Blerina</au><au>Zonta, Cristiano</au><au>Bartik, Kristin</au><au>Cavani, Fabrizio</au><au>Solmi, Stefania</au><au>Bo, Carles</au><au>Licini, Giulia</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Efficient Vanadium‐Catalyzed Aerobic C−C Bond Oxidative Cleavage of Vicinal Diols</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2018-09-03</date><risdate>2018</risdate><volume>360</volume><issue>17</issue><spage>3286</spage><epage>3296</epage><pages>3286-3296</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>The aerobic oxidative C−C bond cleavage of vicinal diols catalyzed by vanadium amino triphenolates is described. Our results show that C−C bond cleavage can be performed in different solvents, under an air or oxygen atmosphere, with a large variety of glycols (cyclic or linear, with aromatic or aliphatic substituents) affording the corresponding carbonyl derivatives with high chemoselectivity. Reactions can be performed with as little as 10 ppm of catalyst reaching TON up to 81,000 and TOFs of up to 4150 h−1. A reaction mechanism, rationalized by density functional theory calculations, is also proposed.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.201800050</doi><tpages>11</tpages><oa>free_for_read</oa></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Aerobic Oxidation Aliphatic compounds Carbonyls Cleavage C−C Activation Density functional theory Diols Homogeneous Catalysis Oxygen Reaction mechanisms Vanadium |
| title | Efficient Vanadium‐Catalyzed Aerobic C−C Bond Oxidative Cleavage of Vicinal Diols |
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