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

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.

Beilstein J. Org. Chem. 2023, 19, 575–581. doi:10.3762/bjoc.19.42

Source: Beilstein Journal of Organic Chemistry - April 27, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: alkylation EDA complex halogens indoles photochemistry Letter Source Type: research