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Direct C2–H alkylation of indoles driven by the photochemical activity of halogen-bonded complexes

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A light-driven metal-free protocol for the synthesis of sulfone-containing indoles under mild conditions is reported. Specifically, the process is driven by the photochemical activity of halogen-bonded complexes formed upon complexation… Click to show full abstract

A light-driven metal-free protocol for the synthesis of sulfone-containing indoles under mild conditions is reported. Specifically, the process is driven by the photochemical activity of halogen-bonded complexes formed upon complexation of a sacrificial donor, namely 1,4-diazabicyclo[2.2.2]octane (DABCO), with α-iodosulfones. The reaction provides a variety of densely functionalized products in good yields (up to 96% yield). Mechanistic investigations are reported. These studies provide convincing evidences for the photochemical formation of reactive open-shell species.

Keywords: photochemical activity; bonded complexes; activity halogen; driven photochemical; halogen bonded

Journal Title: Beilstein Journal of Organic Chemistry
Year Published: 2023

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