Regiocontrolled gold(I)-catalyzed cyclization reactions of N-(3-iodoprop-2-ynyl)-N-tosylanilines

The gold(I)-catalyzed cyclization reactions of N-(3-Iodoprop-2-ynyl)-N-tosylaniline derivatives afford iodinated 1,2-dihydroquinoline derivatives. Two regioisomer products are obtained, one derived from direct cyclization and other involving concomitant 1,2-iodo migration. The ratio of these two products can be modulated by a proper ancillary ligand in the gold catalyst.

The paper discusses the influence of the ligand in the gold catalyst and the electronic character of the substituent in the arene in the product distribution noticed.Figure optionsDownload as PowerPoint slide