Brønsted Acid-Catalyzed Dehydrative Nazarov-Type Cyclization/C2-N1 Cleavage Cascade of Perfluoroalkylated 3-Indolyl(2-benzothienyl)methanols.

A novel and unprecedented p -toluenesulfonic acid-catalyzed dehydrative Nazarov-type cyclization/C2-N1 bond cleavage cascade reaction of perfluoroalkylated 3-indolyl(2-benzothienyl)methanols has been developed. This reaction provides an efficient and practical protocol for the construction of highly functionalized benzothiophene-fused cyclopentenones with exclusive stereoselectivity. In addition, this cascade transformation also delineates a rare example of the involvement of the selective C2-N1 bond cleavage of indoles.