Get access

Palladium-Catalyzed Oxidative Arylating Carbocyclization of Allenynes: Control of Selectivity and Role of H2O

Authors


  • Financial support from the European Research Council (ERC AdG 247014), the Swedish Research Council, the Berzelii Centre EXSELENT, the Knut and Alice Wallenberg Foundation, and the Wenner-Gren Foundation (Y.D.) is gratefully acknowledged. We also thank Tuo Jiang and Abraham Mendoza for valuable discussions.

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.

Get access to the full text of this article

Ancillary