Phosphoric Acid Catalyzed Electrophilic Thiocyanation of Indoles: Access to SCN‐Containing Aryl‐Indole Compounds
Ai‐Hui Ye, Zi‐Hao Li, Tong‐Mei Ding, Hua Ke, Zhi‐Min Chen
Abstract
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.
Topics & Concepts
ArylElectrophileIndole testPhosphoric acidCatalysisChemistryCombinatorial chemistryOrganic chemistryMedicinal chemistryAlkylAxial and Atropisomeric Chirality SynthesisSphingolipid Metabolism and SignalingAlkaloids: synthesis and pharmacology