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Palladium‐Catalyzed Oxidative Borylative Carbocyclization of Enallenes
Author(s) -
Persson Andreas K. Å.,
Jiang Tuo,
Johnson Magnus T.,
Bäckvall JanE.
Publication year - 2011
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.201008032
Subject(s) - borylation , palladium , allene , reagent , catalysis , chemistry , oxidative phosphorylation , boron , combinatorial chemistry , organic chemistry , biochemistry , alkyl , aryl
An efficient oxidative carbocyclization/borylation of enallenes uses Pd(OAc) 2 as the catalyst, B 2 pin 2 as the boron‐transfer reagent, and 1,4‐benzoquinone (BQ) as the oxidant (see scheme). The reaction seems to take place through activation of the allene by a Pd II complex to give an alkenyl–Pd II intermediate followed by carbopalladation of the olefin and subsequent cleavage of the intermediate palladium–carbon bond by the boron reagent.