Photocatalytic Deoxygenative Carboimination towards Functionalized Pyrrolines by Using Unstrained γ,δ‐Unsaturated Oximes
Photocatalytic deoxygenative carboimination of unstrained γ,δ‐unsaturated oximes with π‐acceptors including trifluoromethyl alkenes, 1‐trifluoromethyl‐1,3‐butadienes, gem‐difluoroalkenes, acrylates, and styrenes has been achieved which provides an efficient and mild approach to construct structurall...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2021-04, Vol.363 (8), p.2110-2116 |
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| container_end_page | 2116 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Zhang, Min Zhang, Zhijie He, Yangsen Zou, Ting Qi, Zhongyu Fu, Qiang Wei, Jun Lu, Ji Wei, Siping Yi, Dong |
| description | Photocatalytic deoxygenative carboimination of unstrained γ,δ‐unsaturated oximes with π‐acceptors including trifluoromethyl alkenes, 1‐trifluoromethyl‐1,3‐butadienes, gem‐difluoroalkenes, acrylates, and styrenes has been achieved which provides an efficient and mild approach to construct structurally diverse and highly functionalized pyrrolines with good functional group tolerance. Importantly, upon utilization of trifluoromethyl alkenes as the coupling partners, the developed protocol not only allows the introduction of the extremely valuable gem‐difluoroalkene functionality and pyrroline moiety into one molecule, but could also further transform the resulting gem‐difluoroalkene‐functionalized pyrrolines to the architecturally intriguing indolizine alkaloids via oxidation/reduction and sequential C−F bond cleavage. The mechanistic studies indicated that a free‐radical and anionic process was probably involved in this photocatalytic deoxygenative transformation. |
| doi_str_mv | 10.1002/adsc.202100038 |
| format | Article |
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Importantly, upon utilization of trifluoromethyl alkenes as the coupling partners, the developed protocol not only allows the introduction of the extremely valuable gem‐difluoroalkene functionality and pyrroline moiety into one molecule, but could also further transform the resulting gem‐difluoroalkene‐functionalized pyrrolines to the architecturally intriguing indolizine alkaloids via oxidation/reduction and sequential C−F bond cleavage. The mechanistic studies indicated that a free‐radical and anionic process was probably involved in this photocatalytic deoxygenative transformation.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.202100038</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Acrylates ; Alkenes ; Carboimination ; Deoxygenation ; Functional groups ; Functionalized pyrrolines ; Indolizines ; Oxidation ; Oximes ; Photocatalysis ; Photoredox Catalysis ; Styrenes ; γ,δ-Unsaturated oximes</subject><ispartof>Advanced synthesis & catalysis, 2021-04, Vol.363 (8), p.2110-2116</ispartof><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3178-aef3bbd90ce3e3fff323e4e500e7d0d33e4210c0998c5124b2225e3f121d99cf3</citedby><cites>FETCH-LOGICAL-c3178-aef3bbd90ce3e3fff323e4e500e7d0d33e4210c0998c5124b2225e3f121d99cf3</cites><orcidid>0000-0001-9993-8776</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fadsc.202100038$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.202100038$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Zhang, Min</creatorcontrib><creatorcontrib>Zhang, Zhijie</creatorcontrib><creatorcontrib>He, Yangsen</creatorcontrib><creatorcontrib>Zou, Ting</creatorcontrib><creatorcontrib>Qi, Zhongyu</creatorcontrib><creatorcontrib>Fu, Qiang</creatorcontrib><creatorcontrib>Wei, Jun</creatorcontrib><creatorcontrib>Lu, Ji</creatorcontrib><creatorcontrib>Wei, Siping</creatorcontrib><creatorcontrib>Yi, Dong</creatorcontrib><title>Photocatalytic Deoxygenative Carboimination towards Functionalized Pyrrolines by Using Unstrained γ,δ‐Unsaturated Oximes</title><title>Advanced synthesis & catalysis</title><description>Photocatalytic deoxygenative carboimination of unstrained γ,δ‐unsaturated oximes with π‐acceptors including trifluoromethyl alkenes, 1‐trifluoromethyl‐1,3‐butadienes, gem‐difluoroalkenes, acrylates, and styrenes has been achieved which provides an efficient and mild approach to construct structurally diverse and highly functionalized pyrrolines with good functional group tolerance. Importantly, upon utilization of trifluoromethyl alkenes as the coupling partners, the developed protocol not only allows the introduction of the extremely valuable gem‐difluoroalkene functionality and pyrroline moiety into one molecule, but could also further transform the resulting gem‐difluoroalkene‐functionalized pyrrolines to the architecturally intriguing indolizine alkaloids via oxidation/reduction and sequential C−F bond cleavage. The mechanistic studies indicated that a free‐radical and anionic process was probably involved in this photocatalytic deoxygenative transformation.</description><subject>Acrylates</subject><subject>Alkenes</subject><subject>Carboimination</subject><subject>Deoxygenation</subject><subject>Functional groups</subject><subject>Functionalized pyrrolines</subject><subject>Indolizines</subject><subject>Oxidation</subject><subject>Oximes</subject><subject>Photocatalysis</subject><subject>Photoredox Catalysis</subject><subject>Styrenes</subject><subject>γ,δ-Unsaturated oximes</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFUM1OAjEYbIwmInr13MSrYH9Ylj2SRdSEBBLl3HTbLpYsW2y7whoPPoLvos_BQ_gkdoPRo6fvm8nMl_kGgHOMuhghcsWlE12CSACIDg5AC_dx1OnhfnL4u0foGJw4t0QIx4M4boHX2aPxRnDPi9prAUfKbOuFKrnXzwqm3GZGr3QDTQm92XArHRxXpWgIXugXJeGsttYUulQOZjWcO10u4Lx03vLASbj7uNx9fr29B4r7ynIfuOlWr5Q7BUc5L5w6-5ltMB9fP6S3ncn05i4dTjqChpgdrnKaZTJBQlFF8zynhKqeihBSsUSSBhCeFihJBiLCpJcRQqIgxATLJBE5bYOL_d21NU-Vcp4tTWVDfMdIMJCY9CMUVN29SljjnFU5W1u94rZmGLGmYdY0zH4bDoZkb9joQtX_qNlwdJ_-eb8BEeCFTg</recordid><startdate>20210413</startdate><enddate>20210413</enddate><creator>Zhang, Min</creator><creator>Zhang, Zhijie</creator><creator>He, Yangsen</creator><creator>Zou, Ting</creator><creator>Qi, Zhongyu</creator><creator>Fu, Qiang</creator><creator>Wei, Jun</creator><creator>Lu, Ji</creator><creator>Wei, Siping</creator><creator>Yi, Dong</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0001-9993-8776</orcidid></search><sort><creationdate>20210413</creationdate><title>Photocatalytic Deoxygenative Carboimination towards Functionalized Pyrrolines by Using Unstrained γ,δ‐Unsaturated Oximes</title><author>Zhang, Min ; Zhang, Zhijie ; He, Yangsen ; Zou, Ting ; Qi, Zhongyu ; Fu, Qiang ; Wei, Jun ; Lu, Ji ; Wei, Siping ; Yi, Dong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3178-aef3bbd90ce3e3fff323e4e500e7d0d33e4210c0998c5124b2225e3f121d99cf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Acrylates</topic><topic>Alkenes</topic><topic>Carboimination</topic><topic>Deoxygenation</topic><topic>Functional groups</topic><topic>Functionalized pyrrolines</topic><topic>Indolizines</topic><topic>Oxidation</topic><topic>Oximes</topic><topic>Photocatalysis</topic><topic>Photoredox Catalysis</topic><topic>Styrenes</topic><topic>γ,δ-Unsaturated oximes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Min</creatorcontrib><creatorcontrib>Zhang, Zhijie</creatorcontrib><creatorcontrib>He, Yangsen</creatorcontrib><creatorcontrib>Zou, Ting</creatorcontrib><creatorcontrib>Qi, Zhongyu</creatorcontrib><creatorcontrib>Fu, Qiang</creatorcontrib><creatorcontrib>Wei, Jun</creatorcontrib><creatorcontrib>Lu, Ji</creatorcontrib><creatorcontrib>Wei, Siping</creatorcontrib><creatorcontrib>Yi, Dong</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>Zhang, Min</au><au>Zhang, Zhijie</au><au>He, Yangsen</au><au>Zou, Ting</au><au>Qi, Zhongyu</au><au>Fu, Qiang</au><au>Wei, Jun</au><au>Lu, Ji</au><au>Wei, Siping</au><au>Yi, Dong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photocatalytic Deoxygenative Carboimination towards Functionalized Pyrrolines by Using Unstrained γ,δ‐Unsaturated Oximes</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2021-04-13</date><risdate>2021</risdate><volume>363</volume><issue>8</issue><spage>2110</spage><epage>2116</epage><pages>2110-2116</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>Photocatalytic deoxygenative carboimination of unstrained γ,δ‐unsaturated oximes with π‐acceptors including trifluoromethyl alkenes, 1‐trifluoromethyl‐1,3‐butadienes, gem‐difluoroalkenes, acrylates, and styrenes has been achieved which provides an efficient and mild approach to construct structurally diverse and highly functionalized pyrrolines with good functional group tolerance. Importantly, upon utilization of trifluoromethyl alkenes as the coupling partners, the developed protocol not only allows the introduction of the extremely valuable gem‐difluoroalkene functionality and pyrroline moiety into one molecule, but could also further transform the resulting gem‐difluoroalkene‐functionalized pyrrolines to the architecturally intriguing indolizine alkaloids via oxidation/reduction and sequential C−F bond cleavage. The mechanistic studies indicated that a free‐radical and anionic process was probably involved in this photocatalytic deoxygenative transformation.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.202100038</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0001-9993-8776</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Acrylates Alkenes Carboimination Deoxygenation Functional groups Functionalized pyrrolines Indolizines Oxidation Oximes Photocatalysis Photoredox Catalysis Styrenes γ,δ-Unsaturated oximes |
| title | Photocatalytic Deoxygenative Carboimination towards Functionalized Pyrrolines by Using Unstrained γ,δ‐Unsaturated Oximes |
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