Synthesis of <i>N</i>‐Aryl Isoxazolidines by Photo‐Promoted <i>N</i>‐Selective Arylation of Oximes and Cyclization Using Hypervalent Iodine Reagents and Copper Catalyst
Synthesis of <i>N</i>‐Aryl Isoxazolidines by Photo‐Promoted <i>N</i>‐Selective Arylation of Oximes and Cyclization Using Hypervalent Iodine Reagents and Copper Catalyst
复制标题
使用高价碘试剂和铜催化剂通过光促进肟的<i>N</i>-选择性芳基化和环化合成<i>N</i>-芳基异恶唑烷
DOI：
10.1002/adsc.202300110
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发表时间：
2023
期刊：
影响因子：
--
通讯作者：
III、Yoshida Mayumi、Yamamoto Ayaka、Hashimoto Yoshimitsu、Morita Nobuyoshi、Tamura Osamu
中科院分区：
文献类型：
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作者：
Tanaka Kosaku;III、Yoshida Mayumi、Yamamoto Ayaka、Hashimoto Yoshimitsu、Morita Nobuyoshi、Tamura Osamu
肟类化合物在光催化下与二芳基碘盐进行N-选择性芳基化反应生成硝酮，硝酮与烯烃在分子内或分子间发生1，3-偶极环化反应生成N-芳基异恶唑烷。用富电子或缺电子基团取代的高价碘试剂以26-95%的产率得到相应的N-芳基异恶唑烷。与使用Chan-Lam-Evans偶联的类似的硝酮合成方法相比，该方法具有反应速度快、催化剂负载量低、肟底物范围广等优点。该反应通过自由基/单电子转移(SET)途径进行，在没有光照射的情况下不会进行。
Oximes cause photo‐promoted, copper‐catalyzedN‐selective arylation with diaryl iodonium salts to produce nitrones, which in turn undergo intra‐ or intermolecular 1,3‐dipolar cyclization with olefins to affordN‐aryl isoxazolidines. Hypervalent iodine reagents substituted with either electron‐rich or electron‐deficient groups afford the correspondingN‐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.