1716
K. N. Patel, A. V. Bedekar
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selectivity in favor of Suzuki–Miyaura reaction with active
aryl bromide (Scheme 5).
Many alkoxy substituted derivatives of biphenyl or
biaryl compounds have been studied for their specific
properties. Compounds containing alkoxy functional
groups have been studied as materials with thermal prop-
erties [93–96]. Several compounds possessing alkoxy
substituents and showing liquid crystalline properties [97–
100] are required for appropriate crystal packing and hence
are responsible for the specific thermal behavior. Usually
the introduction of alkoxy substituent is carried out as a
separate specific chemical operation but we have recently
developed a couple of one-pot O-alkylation-Wittig and O-
alkylation-Wittig-Heck reactions to synthesize alkoxy
stilbenes [72]. In this work we have extended the strategy
to synthesize O-alkoxy biphenyls and O-alkoxy biaryls by
simultaneously conducting Suzuki–Miyaura and O-alkyla-
tion reaction on bromo phenols (Scheme 6). As outlined
the three components of this version include bromo phenol,
arylboronic acid and the alkyl halide treated with catalyst
B-2 in presence of suitable base, PTC in aqueous dioxane.
A series of examples were tested to establish this one-
pot reaction and the results are presented in Chart 1.
Consistently good conversions and isolated yields were
observed for the examples studied in this work.
¨
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In conclusion we wish to report application of polymer
anchored amines as heterogeneous ligands for palladium
catalysts for Suzuki–Miyaura coupling reactions of aryl
halides. The yields and TON of our catalytic system for
this reaction were comparable with other heterogeneous
palladium catalysts. The catalyst system was also scanned
for the one-pot O-alkylation-Suzuki combination to syn-
thesize series of alkoxy biaryl systems.
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Acknowledgment We thank Council of Scientific and Industrial
Research (CSIR), New Delhi for a research fellowship to KNP.
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