Palladium-catalyzed oxidative arylating carbocyclization of allenynes: control of selectivity and role of H₂O.

Abstract

Highly selective protocols for the carbocyclization/arylation of allenynes using arylboronic acids are reported. Arylated vinylallenes are obtained with the use of BF3⋅Et2O as an additive, whereas addition of water leads to arylated trienes. These conditions provide the respective products with excellent selectivities (generally >97:3) for a range of boronic acids and different allenynes. It has been revealed that water plays a crucial role for the product distribution.

DOI: 10.1002/anie.201404264