Synthesis of N‐Aryl Isoxazolidines by Photo‐Promoted N‐Selective Arylation of Oximes and Cyclization Using Hypervalent Iodine Reagents and Copper Catalyst
Oximes cause photo‐promoted, copper‐catalyzed N‐selective arylation with diaryl iodonium salts to produce nitrones, which in turn undergo intra‐ or intermolecular 1,3‐dipolar cyclization with olefins to afford N‐aryl isoxazolidines. Hypervalent iodine reagents substituted with either electron‐rich o...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2023-05, Vol.365 (9), p.1419-1424 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Tanaka, Kosaku Yoshida, Mayumi Yamamoto, Ayaka Hashimoto, Yoshimitsu Morita, Nobuyoshi Tamura, Osamu |
| description | Oximes cause photo‐promoted, copper‐catalyzed N‐selective arylation with diaryl iodonium salts to produce nitrones, which in turn undergo intra‐ or intermolecular 1,3‐dipolar cyclization with olefins to afford N‐aryl isoxazolidines. Hypervalent iodine reagents substituted with either electron‐rich or electron‐deficient groups afford the corresponding N‐aryl isoxazolidines in 26–95% yields. This method offers a faster reaction rate, lower catalyst loading and broader substrate scope of oxime than similar nitrone syntheses employing Chan‐Lam‐Evans coupling. The reaction involves via a radical/single electron transfer (SET) pathway, and does not proceed in the absence of photoirradiation. |
| doi_str_mv | 10.1002/adsc.202300110 |
| format | Article |
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Hypervalent iodine reagents substituted with either electron‐rich or electron‐deficient groups afford the corresponding N‐aryl isoxazolidines in 26–95% yields. This method offers a faster reaction rate, lower catalyst loading and broader substrate scope of oxime than similar nitrone syntheses employing Chan‐Lam‐Evans coupling. 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The reaction involves via a radical/single electron transfer (SET) pathway, and does not proceed in the absence of photoirradiation.</description><subject>Alkenes</subject><subject>Aromatic compounds</subject><subject>Catalysts</subject><subject>Copper</subject><subject>Cyclization</subject><subject>Electron transfer</subject><subject>Iodine</subject><subject>Isoxazolidines</subject><subject>N ligand</subject><subject>Oximes</subject><subject>Photochemistry</subject><subject>Reagents</subject><subject>Single electrons</subject><subject>Substrates</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqFkbtOwzAUhiMEEqWwMltiTrGdi52xCpdWQhRRmCMnPQajNA62WxomHoFH4Nl4EhyKYGSyj873_Wf4g-CY4BHBmJ6Kha1GFNMIY0LwTjAgKUnCmKTZ7u8_wfvBgbVPHmGcsUHwMe8a9whWWaQluv58ex-brkZTqzfiVddqoRqwqOzQzaN22q9vjF5qB4tvdg41VE6tAfWWcEo3fcxso5beEs0C5V1Vq9ft5t6q5gFNuhbMWtTQODTVfT66BfHgxx9Dtx5AuXCi7qw7DPakqC0c_bzD4P7i_C6fhFezy2k-vgqriEc4TKTAUcliyDKISEkzLMuYx6zigvIkxZhJP1FCBZMiI5ASSFgmS0aEBJbG0TA42ea2Rj-vwLriSa9M408WlBPKeUJ46qnRlqqMttaALFqjlsJ0BcFF30LRt1D8tuCFbCu8qBq6f-hifDbP_9wvPgeQvw</recordid><startdate>20230512</startdate><enddate>20230512</enddate><creator>Tanaka, Kosaku</creator><creator>Yoshida, Mayumi</creator><creator>Yamamoto, Ayaka</creator><creator>Hashimoto, Yoshimitsu</creator><creator>Morita, Nobuyoshi</creator><creator>Tamura, Osamu</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/0000-0002-3591-5409</orcidid></search><sort><creationdate>20230512</creationdate><title>Synthesis of N‐Aryl Isoxazolidines by Photo‐Promoted N‐Selective Arylation of Oximes and Cyclization Using Hypervalent Iodine Reagents and Copper Catalyst</title><author>Tanaka, Kosaku ; Yoshida, Mayumi ; Yamamoto, Ayaka ; Hashimoto, Yoshimitsu ; Morita, Nobuyoshi ; Tamura, Osamu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3830-5fa03b74e99e31b290fb4847c8a2856007f847212a7fa91e61e579fb71afe7643</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Alkenes</topic><topic>Aromatic compounds</topic><topic>Catalysts</topic><topic>Copper</topic><topic>Cyclization</topic><topic>Electron transfer</topic><topic>Iodine</topic><topic>Isoxazolidines</topic><topic>N ligand</topic><topic>Oximes</topic><topic>Photochemistry</topic><topic>Reagents</topic><topic>Single electrons</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tanaka, Kosaku</creatorcontrib><creatorcontrib>Yoshida, Mayumi</creatorcontrib><creatorcontrib>Yamamoto, Ayaka</creatorcontrib><creatorcontrib>Hashimoto, Yoshimitsu</creatorcontrib><creatorcontrib>Morita, Nobuyoshi</creatorcontrib><creatorcontrib>Tamura, Osamu</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>Tanaka, Kosaku</au><au>Yoshida, Mayumi</au><au>Yamamoto, Ayaka</au><au>Hashimoto, Yoshimitsu</au><au>Morita, Nobuyoshi</au><au>Tamura, Osamu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of N‐Aryl Isoxazolidines by Photo‐Promoted N‐Selective Arylation of Oximes and Cyclization Using Hypervalent Iodine Reagents and Copper Catalyst</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2023-05-12</date><risdate>2023</risdate><volume>365</volume><issue>9</issue><spage>1419</spage><epage>1424</epage><pages>1419-1424</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>Oximes cause photo‐promoted, copper‐catalyzed N‐selective arylation with diaryl iodonium salts to produce nitrones, which in turn undergo intra‐ or intermolecular 1,3‐dipolar cyclization with olefins to afford N‐aryl isoxazolidines. 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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alkenes Aromatic compounds Catalysts Copper Cyclization Electron transfer Iodine Isoxazolidines N ligand Oximes Photochemistry Reagents Single electrons Substrates |
| title | Synthesis of N‐Aryl Isoxazolidines by Photo‐Promoted N‐Selective Arylation of Oximes and Cyclization Using Hypervalent Iodine Reagents and Copper Catalyst |
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