Palladium(II)-Catalyzed Intramolecular C-H Alkenylation for the Synthesis of Chromanes.

Abstract

The intramolecular Pd(II)-catalyzed alkenylation of aryl homoallyl ethers constitutes a mild, versatile, and efficient procedure for the synthesis of highly and diversely substituted chromanes and 2 H-chromenes. The use of p-TsOH as an additive allows more efficient reactions that could be carried out a room temperature in most cases. The procedure has a wide scope, allowing the synthesis of alkylidenechromanes and 2 H-chromenes substituted at C-2 or C-3 of the chromene moiety, thus accessing relevant flavenes and isoflavenes, and even coumarins, in high yields (59 to 91%, 32 examples).