Brønsted Acid-Catalyzed Dehydrative Nazarov-type Cyclization of CF 3 -Substituted 3-Indolylallyl Alcohols: Divergent Synthesis of 1-Trifluoromethylated Cyclopenta[ b ]indoles.

An expedient and efficient synthetic method for the divergent synthesis of 1-trifluoromethylated cyclopenta[ b ]indoles that relies on Brønsted acid-catalyzed dehydrative Nazarov-type cyclization of CF3 -substituted 3-indolylallyl alcohols is described. Two classes of 1-trifluoromethylated cyclopenta[ b ]indoles can be easily accessed simply by changing the NH-protecting group of indoles. With arylsulfonyl protected 3-indolylallyl alcohols as starting materials, the reaction provided the arylsulfonyl protected 1-trifluoromethylated cyclopenta[ b ]indoles in good to excellent yields, whereas pivaloyl (Piv) protected substrates led to the formation of NH-free 1-trifluoromethylated cyclolopenta[ b ]indoles with another alkenyl isomer. This protocol features tunable chemoselectivity, operational simplicity, excellent functional group compatibility, and mild metal-free conditions.