Bugaenko Dmitry I, Malashchenko Nikolai A, Kopytov Sergei O, Lukonina Natalia S, Karchava Alexander V
Department of Chemistry, Moscow State University, Moscow 119991, Russia.
Org Lett. 2024 Apr 19;26(15):3189-3194. doi: 10.1021/acs.orglett.4c00797. Epub 2024 Apr 8.
A new umpolung approach to the C-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.
