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(Indol-3-yl)(DMIX)Iodonium Salts: Novel Electrophilic Indole Reagents
Organic Letters ( IF 4.9 ) Pub Date : 2024-04-08 , DOI: 10.1021/acs.orglett.4c00797 Dmitry I Bugaenko 1 , Nikolai A Malashchenko 1 , Sergei O Kopytov 1 , Natalia S Lukonina 1 , Alexander V Karchava 1
Organic Letters ( IF 4.9 ) Pub Date : 2024-04-08 , DOI: 10.1021/acs.orglett.4c00797 Dmitry I Bugaenko 1 , Nikolai A Malashchenko 1 , Sergei O Kopytov 1 , Natalia S Lukonina 1 , Alexander V Karchava 1
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A new umpolung approach to the C3–H functionalization of indoles with diverse nucleophiles based on the intermediate formation of I(III) reagents is described. The 3,5-dimethylisoxazol-4-yl auxiliary allows for selective indole transfer under catalyst-free conditions, which was impossible using previously reported reagents. Combining the mildness of transition-metal-free conditions and the high reactivity of hypervalent iodine reagents, this protocol tolerates various functional groups and provides access to indoles that are difficult to prepare conventionally.
中文翻译：
(Indol-3-yl)(DMIX)碘鎓盐：新型亲电吲哚试剂
描述了一种基于 I(III) 试剂中间形成的吲哚 C 3 –H 功能化的新方法。 3,5-二甲基异恶唑-4-基助剂允许在无催化剂条件下选择性吲哚转移，这是使用先前报道的试剂不可能实现的。该方案结合了无过渡金属条件的温和性和高价碘试剂的高反应性，可耐受各种官能团，并提供了常规难以制备的吲哚的途径。
更新日期：2024-04-08
中文翻译：
(Indol-3-yl)(DMIX)碘鎓盐：新型亲电吲哚试剂
描述了一种基于 I(III) 试剂中间形成的吲哚 C 3 –H 功能化的新方法。 3,5-二甲基异恶唑-4-基助剂允许在无催化剂条件下选择性吲哚转移，这是使用先前报道的试剂不可能实现的。该方案结合了无过渡金属条件的温和性和高价碘试剂的高反应性，可耐受各种官能团，并提供了常规难以制备的吲哚的途径。
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