A mild and simple electrochemical system has been developed for efficient cyclization of 2-ethynylanilines, employing potassium iodide as the only additive in a non-volatile aqueous solvent. Notably, by altering the electrode material and charge passed, either 3-iodoindoles or indoles can be selectively furnished in high efficiency with broad substrate scope and good functional group compatibility. The synthetic potential is demonstrated with several examples of late-stage functionalization, gram-scale synthesis and further derivatization. Mechanistic studies reveal that apart from the key anodic events, cathodic generation of base (HO–) from water reduction also plays a crucial role in these efficient conversions.

You have access to this article

Please wait while we load your content... Something went wrong. Try again?