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Aryl–Aryl Bond Formation by the Fluoride‐Free Cross‐Coupling of Aryldisiloxanes with Aryl Bromides
Author(s) -
Boehner Christine M.,
Frye Elizabeth C.,
O'Connell Kieron M. G.,
Galloway Warren R. J. D.,
Sore Hannah F.,
Dominguez Patricia Garcia,
Norton David,
Hulcoop David G.,
Owen Martin,
Turner Gillian,
Crawford Claire,
Horsley Helen,
Spring David R.
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201102285
Subject(s) - aryl , combinatorial chemistry , molecule , fluoride , chemistry , palladium , computational chemistry , organic chemistry , catalysis , inorganic chemistry , alkyl
Abstract The prevalence of the biaryl structural motif in biologically interesting and synthetically important molecules has inspired considerable interest in the development of methods for aryl–aryl bond formation. Herein we describe a novel strategy for this process involving the fluoride‐free, palladium‐catalysed cross‐coupling of readily accessible aryldisiloxanes and aryl bromides. Using a statistical‐based optimisation process, preparatively useful reaction conditions were formulated to allow the cross‐coupling of a wide range of different substrates. This methodology represents an attractive, cost‐efficient, flexible and robust alternative to the traditional transition‐metal‐catalysed routes typically used to generate molecules containing the privileged biaryl scaffold.