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Exploiting Boron–Zinc Transmetallation for the Arylation of Benzyl Halides: What are the Reactive Species?
Author(s) -
Bedford Robin B.,
Gower Nicholas J.,
Haddow Mairi F.,
Harvey Jeremy N.,
Nunn Joshua,
Okopie Rukeme A.,
Sankey Rosalind F.
Publication year - 2012
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.201202219
Subject(s) - transmetalation , electrophile , chemistry , zinc , halide , boron , reactive intermediate , combinatorial chemistry , class (philosophy) , solvent , medicinal chemistry , computer science , organic chemistry , catalysis , artificial intelligence
One step B eyond : The transmetallation reactions of ArB(OH) 2 and Ar 3 B 3 O 3 with Et 2 Zn are far more complicated than previously supposed, with solvent‐dependent equilibria between ArB(OY) 2 at one side and [RZn(solv) 3 ][BR 4 ] at the other (see picture). While the role of the highly reactive organozinc cation has not been implicated before, its importance for the activation of an otherwise sluggish class of electrophiles is shown.