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Control of Selectivity in Palladium‐Catalyzed Oxidative Carbocyclization/Borylation of Allenynes
Author(s) -
Deng Youqian,
Bartholomeyzik Teresa,
Bäckvall JanE.
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201301167
Subject(s) - borylation , chemistry , palladium , catalysis , hydroboration , combinatorial chemistry , reagent , allylic rearrangement , organic chemistry , aryl , alkyl
In control : A highly selective carbocyclization/borylation of allenynes with bis(pinacolato)diboron (B 2 pin 2 ) under palladium catalysis and with p ‐benzoquinone (BQ) as the oxidant was developed. The use of either LiOAc⋅2 H 2 O with 1,2‐dichloroethane (DCE) as the solvent or BF 3 ⋅Et 2 O together with THF is crucial for the selective formation of borylated trienes and vinylallenes, respectively.