The selective control over multiple competing C–H sites would enable straightforward access to functionalized indoles. In this context, we report here a modular and selective C–H arylation of indoles via the micellar catalysis approach using the third generation “designer” surfactant SPGS-550-M in the presence of 1 mol % of [(cinnamyl)PdCl]2 under mild conditions. Thus, access to high value C-arylated (C-3 and C-2) indoles was achieved fulfilling the “triple bottom line philosophy” of green chemistry. The nature of the phosphine ligand was found to be critical for achieving site-selectivity, DPPF and DPPP being the most effective in promoting the arylation at C3–H and C2–H, respectively. The reaction is scalable and offers high chemo- (C vs. N) and regio-selectivity (C-3 vs. C-2) with a wide range of functional group tolerance. The surfactant aqueous solution can be recycled and reused without compromising on product yields.

Sustainable synthesis of 2/3-aryl indoles under Pd-catalysis in SPGS-550-M micellar medium

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.