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Green Chemistry
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Journal Name
ARTICLE
DOI: 10.1039/C9GC03455B
2004, 43, 9664-9673.
Conclusion
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R. Loska, Ch. M. Volla and P. Vogel, Adv. Synth. Catal., 2008, 350,
2859-2864.
W. Li-xia, W. Zi-wei, W. Guo-song, L. Xiao-dong and R. Jian-guo.
In this paper, a new hydrophilic heterogeneous cobalt catalyst of
chitosan-Schiff base, containing mono-methoxytriethylene glycol
(mTEG) as a phase transfer functional group, was introduced. This
newly synthesized catalyst was characterized by different methods
such as XRD, FE-SEM, TEM, TGA, FT-IR, 13C{1H} CP/MAS NMR, XPS and
ICP analysis and used efficiently as a heterogeneous catalyst in C-C
and C(sp2)–P cross-coupling reactions such as palladium and fluoride-
free Hiyama, Suzuki, Heck and Hirao reactions in water. A wide range
of aryliodides, bromides and chlorides (the most challenging
arylhalides which are much cheaper and more widely available than
aryl iodides and bromides) was coupled successfully with
triethoxyphenylsilane, phenylboronic acid, alkyl acrylates, styrene
and triethylphosphite to generate the corresponding products. By this
method, good to high yields of the products were achieved in water
as a benign solvent without the need of any additive or organic
solvents. Notably, this is the first report on the application of a cobalt
catalyst in the Hiyama reaction. Any further conversion in the
remaining solution after separation of the catalyst in the hot filtration
test and poisoning test using S8 showed that the observed catalysis
was heterogeneous in nature. Due to the extremely low solubility of
the catalyst in organic solvents, the separated aqueous phase which
contains the catalyst can be readily recycled for six sequential runs
without a noteworthy loss in activity. Finally, the catalyst can be
simply isolated from the aqueous layer by filtration. Using water as a
green solvent without requiring any additive or organic solvent, low
cost and abundant cobalt catalyst instead of expensive Pd catalysts,
facile catalyst recovery and scalability make this method favourable
from the environmental and economic point of view for the C-C and
C(sp2)–P cross-coupling reactions.
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248, 17-20.
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S. Ganesh Babu, N. Neelakandeswari, N. Dharmaraj, S. David
Jackson and R. Karvembu. RSC Adv., 2013, 3, 7774-7781.
A. Hajipour and Gh. Azizi, Green Chem., 2013, 15, 1030-1034.
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b) M. Shao, K. Peng, J. Chen, H. Li, X. Wang, W. Zhang and H. Qi,
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Khorsandi, Catal. Commun., 2016, 77, 1-4. d) A. R. Hajipour, F.
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L. Mahesh Kumar, Appl. Organomet. Chem., 2017, 827, 41-48. i)
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Conflicts of interest
10 D. J. Macquarrie and J. J. E. Hardy, Ind. Eng. Chem. Res., 2005, 44,
8499–8520.
11 a) N. V. Majeti and R. Kumar, React. Funct. Polym., 2000, 46, 1-
27. b) T. A. Ahmed and B. M. Aljaeid, Drug Des. Devel. Ther., 2016,
10, 483-507. c) J. Desbrieres and E. Guibal, Polym. Int., 2018, 67,
7-14. d) G. Yuan, X. Chen and D. Li, Food Res. Int., 2016, 89, 117-
128. e) A. Verlee, S. Mincke and Ch. V. Stevens, Carbohyd. Polym.,
2017, 164, 268-283.
12 a) W. Lia-xia, W. Zi-wei, W. Guo-song, L. Xiao-dong and R. Jian-
guo, Polym. Adv. Technol. 2010, 21, 244–249. b) S. M. Alshehri, T.
Almuqati, N. Almuqati, E. Al-Farraj, N. Alhokbany, T. Ahmad,
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Azadi, Appl. Organomet. Chem., 2017, 32, 3906-3915. d) A. Fakhri
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Kh. Khalili and H.M. Al-Matar, Molecules 2013, 18, 5288-5305. f)
M. Zeng, X. Yuan, Sh. Zuo and Ch. Qi, RSC Adv., 2015, 5, 37995-
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There are no conflicts to declare.
Acknowledgements
Financial support of this project by University of Birjand Research
Council and Iran National Science Foundation (INSF) is acknowledged.
Access to the Solid-State NMR facilities at the Department of
Chemistry, Aarhus University and the XPS facilities of University of
Alicante is appreciated.
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