A new type of sp3-like N-centered radical has been generated by selective energy transfer catalysis. Upon photoexcitation, homolytic N–O bond cleavage of N-indolyl carbonate in the presence of an Ir complex produced N- and O-centered radicals. The high spin density at the C3 position of indole led to radical recombination with the O-centered radical, affording valuable 3-oxyindole derivatives without decarboxylation. Transformations of the desired products into various molecules were also demonstrated.

Control over chemo- and regioselectivity is a critical issue in the heterobiaryl synthesis via C-H oxidative coupling. To address this challenge, a strategy to invert the normal polarity of indoles...

A synthetic protocol for the synthesis of C2‐substituted N‐hydroxyindoles has been developed which consists of Sonogashira coupling, partial reduction of the nitro group, and Larock cyclization. This protocol features superior generality and efficiency over conventional alternatives.

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