Electrochemical aerobic Wacker-type oxygenation of triaryl substituted alkenes to 1,2,2-triarylethanones
An effective synthetic approach for various 1,2,2-triarylethanones from triaryl substituted alkenes has been developed via an electrochemical Wacker-type oxygenation with O 2 as the sole oxygen source. It presents the first instance of the Wacker-type oxidation expanding its substrate scope to trisu...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2024-03, Vol.6 (22), p.335-338 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Zhang, Zhou Li, Jin Cai, Zhiwei Kang, Songyao Wang, Jian Cui, Yue Han, Siyuan Sheng, Lei Yin, Qing Dai, Ang Zhao, Weining Zhao, Fangyuan |
| description | An effective synthetic approach for various 1,2,2-triarylethanones from triaryl substituted alkenes has been developed
via
an electrochemical Wacker-type oxygenation with O
2
as the sole oxygen source. It presents the first instance of the Wacker-type oxidation expanding its substrate scope to trisubstituted alkenes. The approach is transition-metal-free, compatible with various functional groups, and can be carried out under mild conditions resulting in satisfactory yields. Mechanistic experiments suggest the C&z.dbd;O bond formation occurs through reactions between cationic carbon species and the superoxide radical, which involves the 1,2-shift of the electron-rich substituent.
An electrochemical oxygenation approach to obtain 1,2,2-triarylethanones represents the first expansion of Wacker-type oxidation substrate scope to triaryl-substituted alkenes. |
| doi_str_mv | 10.1039/d3cc05770d |
| format | Article |
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via
an electrochemical Wacker-type oxygenation with O
2
as the sole oxygen source. It presents the first instance of the Wacker-type oxidation expanding its substrate scope to trisubstituted alkenes. The approach is transition-metal-free, compatible with various functional groups, and can be carried out under mild conditions resulting in satisfactory yields. Mechanistic experiments suggest the C&z.dbd;O bond formation occurs through reactions between cationic carbon species and the superoxide radical, which involves the 1,2-shift of the electron-rich substituent.
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via
an electrochemical Wacker-type oxygenation with O
2
as the sole oxygen source. It presents the first instance of the Wacker-type oxidation expanding its substrate scope to trisubstituted alkenes. The approach is transition-metal-free, compatible with various functional groups, and can be carried out under mild conditions resulting in satisfactory yields. Mechanistic experiments suggest the C&z.dbd;O bond formation occurs through reactions between cationic carbon species and the superoxide radical, which involves the 1,2-shift of the electron-rich substituent.
An electrochemical oxygenation approach to obtain 1,2,2-triarylethanones represents the first expansion of Wacker-type oxidation substrate scope to triaryl-substituted alkenes.</description><subject>Alkenes</subject><subject>Functional groups</subject><subject>Oxidation</subject><subject>Oxygenation</subject><subject>Substitutes</subject><subject>Substrates</subject><subject>Transition metals</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpd0c9P2zAUB3ALgYAxLtxBlnaZJjISO_51nNpuICFxAcEtcl5eaNo0LrYjrf_9DC1Mwhdbeh89vfc1IWdF_rPIublqOEAulMqbPXJccFlmotRP-69vYTLFS3FEvoSwyNMphD4kR1zzUkvFjsl81iNE72COqw5sTy16V3dAHy0s0Wdxs0bq_m6ecbCxcwN1LY2-s37T0zDWIXZxjNhQ2y9xwECjo8Ulu2TZDmGc28Glyldy0No-4OnuPiEPv2f3k-vs9u7PzeTXbQbMyJiVILkxLatZDa1WULYmDVooBW2jpGqEbJRqAdDogueMlZqhrqUoJeMSRc1PyPdt37V3LyOGWK26ANj3dkA3hooZJnNlhNSJfvtEF270Q5ouKSEYM0aYpH5sFXgXgse2WvtulXarirx6zb-a8snkLf9pwhe7lmO9wuaDvgeewPkW-AAf1f8fyP8B96iKPQ</recordid><startdate>20240312</startdate><enddate>20240312</enddate><creator>Zhang, Zhou</creator><creator>Li, Jin</creator><creator>Cai, Zhiwei</creator><creator>Kang, Songyao</creator><creator>Wang, Jian</creator><creator>Cui, Yue</creator><creator>Han, Siyuan</creator><creator>Sheng, Lei</creator><creator>Yin, Qing</creator><creator>Dai, Ang</creator><creator>Zhao, Weining</creator><creator>Zhao, Fangyuan</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0009-0005-8619-0726</orcidid><orcidid>https://orcid.org/0000-0002-9225-4600</orcidid></search><sort><creationdate>20240312</creationdate><title>Electrochemical aerobic Wacker-type oxygenation of triaryl substituted alkenes to 1,2,2-triarylethanones</title><author>Zhang, Zhou ; Li, Jin ; Cai, Zhiwei ; Kang, Songyao ; Wang, Jian ; Cui, Yue ; Han, Siyuan ; Sheng, Lei ; Yin, Qing ; Dai, Ang ; Zhao, Weining ; Zhao, Fangyuan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c296t-4c6399f2b2bcf87c4f9867177cfd767d56d77fcce9813022482e8b6546236e5b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Alkenes</topic><topic>Functional groups</topic><topic>Oxidation</topic><topic>Oxygenation</topic><topic>Substitutes</topic><topic>Substrates</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Zhou</creatorcontrib><creatorcontrib>Li, Jin</creatorcontrib><creatorcontrib>Cai, Zhiwei</creatorcontrib><creatorcontrib>Kang, Songyao</creatorcontrib><creatorcontrib>Wang, Jian</creatorcontrib><creatorcontrib>Cui, Yue</creatorcontrib><creatorcontrib>Han, Siyuan</creatorcontrib><creatorcontrib>Sheng, Lei</creatorcontrib><creatorcontrib>Yin, Qing</creatorcontrib><creatorcontrib>Dai, Ang</creatorcontrib><creatorcontrib>Zhao, Weining</creatorcontrib><creatorcontrib>Zhao, Fangyuan</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Zhou</au><au>Li, Jin</au><au>Cai, Zhiwei</au><au>Kang, Songyao</au><au>Wang, Jian</au><au>Cui, Yue</au><au>Han, Siyuan</au><au>Sheng, Lei</au><au>Yin, Qing</au><au>Dai, Ang</au><au>Zhao, Weining</au><au>Zhao, Fangyuan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Electrochemical aerobic Wacker-type oxygenation of triaryl substituted alkenes to 1,2,2-triarylethanones</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2024-03-12</date><risdate>2024</risdate><volume>6</volume><issue>22</issue><spage>335</spage><epage>338</epage><pages>335-338</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>An effective synthetic approach for various 1,2,2-triarylethanones from triaryl substituted alkenes has been developed
via
an electrochemical Wacker-type oxygenation with O
2
as the sole oxygen source. It presents the first instance of the Wacker-type oxidation expanding its substrate scope to trisubstituted alkenes. The approach is transition-metal-free, compatible with various functional groups, and can be carried out under mild conditions resulting in satisfactory yields. Mechanistic experiments suggest the C&z.dbd;O bond formation occurs through reactions between cationic carbon species and the superoxide radical, which involves the 1,2-shift of the electron-rich substituent.
An electrochemical oxygenation approach to obtain 1,2,2-triarylethanones represents the first expansion of Wacker-type oxidation substrate scope to triaryl-substituted alkenes.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>38348672</pmid><doi>10.1039/d3cc05770d</doi><tpages>4</tpages><orcidid>https://orcid.org/0009-0005-8619-0726</orcidid><orcidid>https://orcid.org/0000-0002-9225-4600</orcidid></addata></record> |
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| ispartof | Chemical communications (Cambridge, England), 2024-03, Vol.6 (22), p.335-338 |
| issn | 1359-7345 1364-548X |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Alkenes Functional groups Oxidation Oxygenation Substitutes Substrates Transition metals |
| title | Electrochemical aerobic Wacker-type oxygenation of triaryl substituted alkenes to 1,2,2-triarylethanones |
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