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

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 exce...

Full description

Saved in:
Bibliographic Details
Published inAngewandte Chemie (International ed.) Vol. 53; no. 33; pp. 8696 - 8699
Main Authors Bartholomeyzik, Teresa, Mazuela, Javier, Pendrill, Robert, Deng, Youqian, Bäckvall, Jan-E.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 11.08.2014
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
allenes
boronic acids
Chemistry
Chemistry, Multidisciplinary
cyclization
oxidation
palladium
Physical Sciences
Science & Technology
CARBON
DIARYLATING CARBOCYCLIZATION
oxidation
BOND FORMATION
cyclization
ENALLENES
FUNCTIONALIZATION
OXYGEN
allenes
ACTIVATED ALKENES
SUBSTITUTED OLEFINS
OXIDANT
palladium
DERIVATIVES
boronic acids
Online AccessGet full text

Cover

More Information
Summary: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. 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 BF3⋅Et2O whereas the latter product is selectively formed when water is used as an additive. Water plays a crucial role for the product distribution.
Bibliography: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.
Knut and Alice Wallenberg Foundation
istex:B4E12AAF44C1CB1948779C12CE96ED975AD8D044
Berzelii Centre EXSELENT
ArticleID:ANIE201404264
Wenner-Gren Foundation
Swedish Research Council
ark:/67375/WNG-SXRWJNND-Z
European Research Council - No. ERC AdG 247014
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.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201404264