Palladium‐Catalyzed Oxidative Arylating Carbocyclization of Allenynes: Control of Selectivity and Role of H 2 O | Zendy

Bartholomeyzik Teresa | Zendy; Mazuela Javier | Zendy; Pendrill Robert | Zendy; Deng Youqian | Zendy; Bäckvall JanE. | Zendy

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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.

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