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Palladium‐Catalyzed Oxidative Arylating Carbocyclization of Allenynes: Control of Selectivity and Role of H 2 O
Author(s) -
Bartholomeyzik Teresa,
Mazuela Javier,
Pendrill Robert,
Deng Youqian,
Bäckvall JanE.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201404264
Subject(s) - palladium , catalysis , chemistry , selectivity , oxidative phosphorylation , combinatorial chemistry , product distribution , organic chemistry , biochemistry
Highly selective protocols for the carbocyclization/arylation of allenynes using arylboronic acids are reported. Arylated vinylallenes are obtained with the use of BF 3 ⋅Et 2 O 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.