American Chemical Society
ol2c02537_si_002.pdf (17.05 MB)

Palladium-Catalyzed Direct C–H Glycosylation of Free (N‑H) Indole and Tryptophan by Norbornene-Mediated Regioselective C–H Activation

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journal contribution
posted on 2022-09-27, 12:36 authored by Neha Singh Chauhan, Atul Dubey, Pintu Kumar Mandal
We describe the palladium-catalyzed direct C–H glycosylation of free N-H indole or tryptophan for the stereoselective synthesis of 2-glycosylindoles and tryptophan-C-glycosides. This reaction relies on the ortho-directing transient mediator norbornene, which underwent regioselective C–H functionalization at the indole or tryptophan ring, providing high chemoselectivity. This method offers a more straightforward, step-economical, and cost-effective route to construct C-glycosides. The gram-scale amenable building blocks can be further functionalized at C3 and N-H, displaying the robustness of present method.