Palladium-Catalyzed Oxidative Arylating Carbocyclization of Allenynes: Control of Selectivity and Role of H sub(2)O

Highly selective protocols for the carbocyclization/arylation of allenynes using arylboronic acids are reported. Arylated vinylallenes are obtained with the use of BF sub(3)Et sub(2)O as an additive, whereas addition of water leads to arylated trienes. These conditions provide the respective product...

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Published inAngewandte Chemie International Edition Vol. 53; no. 33; pp. 8696 - 8699
Main Authors Bartholomeyzik, Teresa, Mazuela, Javier, Pendrill, Robert, Deng, Youqian, Baeckvall, Jan-E
Format Journal Article
LanguageEnglish
Published 01.08.2014
Subjects
Additives
Formations
Selectivity
Trienes
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Summary:Highly selective protocols for the carbocyclization/arylation of allenynes using arylboronic acids are reported. Arylated vinylallenes are obtained with the use of BF sub(3)Et sub(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. Selective protocols are described for the carbocyclization/arylation of allenynes using arylboronic acids that allow for the formation of either arylated vinylallenes or arylated trienes. Formation of the former product is promoted by the use of BF sub(3)Et sub(2)O whereas the latter product is selectively formed when water is used as an additive. Water plays a crucial role for the product distribution.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201404264