A phosphoric acid catalyzed electrophilic thiocyanation of 3-aryl indoles, which provides an efficient and modular approach to SCN-containing 3-aryl indole compounds, was developed for the first time. A variety of 2-SCN-3-aryl indoles were obtained with moderate to excellent yields. Furthermore, catalytic asymmetric manner of this reaction was also studied. Using chiral phosphoric acid as the catalyst, axially chiral SCN-containing 3-aryl indoles were obtained in moderate to good yields with moderate enantioselectivity.
Keywords: SCN-containing 3-aryl indole; atroposelective; electrophilic thiocyanation; phosphoric acid catalysis; self-disproportionation effect.
© 2022 Wiley-VCH GmbH.