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New Journal of Chemistry
Journal Name
ARTICLE
DOI: 10.1039/C8NJ03708F
stirred at room temperature for 8 h. Next, the solvents were
evaporated under vacuum, and 3 mL of water added into the
tube. Then the aqueous solution was extracted with CH Cl (3
2
2
mL three times). The combined organic phase was dried over
anhydrous MgSO4 and concentrated, and the residue was
purified by column chromatography using petroleum
ether/ethyl acetate (v/v=20:1) as an eluent. Evaporation of the
volatiles under vacuum resulted in the corresponding product.
Fig.3 Recycling of Cu-CuFe O -catalyst for the synthesis of 4.3 Procedure for catalyst recycling
2
4
vinylboronates (Reaction conditions: Phenylacetylene (16 The recycling of the catalyst was carried out for the synthesis
mmol), B Pin (17.6 mmol), Cu-CuFe O nanoparticles (24mg, of vinylboronate under the same procedure given in the
2
2
2
4
0
.5 mol%), MeONa ( 10 mol%), ethanol (20 mL), under Air, section 3.2 under reaction conditions: Phenylacetylene (16
room temperature, t =8h.)
mmol), B Pin (17.6 mmol), Cu-CuFe nanoparticles (24mg,
.5 mol%), MeONa ( 10 mol%), ethanol (20 mL), under air,
O
2 4
2
2
0
room temperature, t = 8h. In each run, after the reaction the
catalyst was separated by filtration, washed thoroughly with
ethyl acetate, water, ethanol and dried by vacuum. Then, the
dried catalyst was used further, without any purification or
reactivation. The filtrate was evaporated under vacuum, and
the residue was purified by column chromatography.
The main text of the article should appear here with headings
as appropriate.
3
. Conclusions
In summary, a Cu-CuFe O NPs was prepared and utilized as a
2
4
highly efficient and environmentally friendly catalyst for the
hydroboration of alkynes. Broad functional group tolerance
and good to excellent yields with high selectivities were
observed under mild conditions. The catalyst shows good
recyclability and can be recovered simply by a magnetic field
and reused six times without significant loss in its catalytic
activities. Furthermore, the heterogeneous catalytic
mechanism was also discussed.
Conclusions
The conclusions section should come in this section at the end
of the article, before the acknowledgements.
4
. Experimental
Materials and instrumentation. Copper(II) chloride dihydrate
CuCl ·2H O), ferric chloride hexahydrate (FeCl ·6H O), sodium
Conflicts of interest
(
2
2
3
2
acetate(NaAC), trisodium citrate dihydrate (Na Cit), The authors declare no conflict of interest.
3
ethyleneglycol (EG), bis(pinacolato)diboron (B Pin ), sodium
2
2
methoxide and all alkenes were purchased from Energy
Chemical Reagent Company. Petroleum ether, ethyl acetate
and other compounds were supplied by Sinopharm Chemical
Reagent Co., Ltd. All reagents used in this work were used
Acknowledgements
Financial support from the National Natural Science
without further purification. The NMR spectra were recorded Foundation of China (21771088, 21371078, 21401077), the
on an Varian 400 MHz spectrometer. GC-MS analysis was Natural Science Foundation of Zhejiang Province
performed on Agilent7890-5975c G3440A 7890 instrument.
(
LY17B030011) and the open research fund of FJIRSM, CAS
20170034) is gratefully acknowledged.T
(
4.1 Procedure for the preparation of Cu-CuFe O catalysts
FeCl ·6H O (4.050 g, 15 mmol), CuCl ·2H O (1.4488 g, 8.5
2
4
3
2
2
2
mmol), NaAc (8.2 g, 100 mmol), and Na Cit (26.1 mg, 0.1 mmol) Notes and references
3
were dissolved in ethylene glycol (100 mL). After the mixture
was stirred at room temperature for 4 h, the obtained
homogeneous solution was transferred to an autoclave and
o
heated to 200 C for 12 h. When the reaction was completed
1
(a) N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457; (b)
T. R. Wu and M. J. Chong, J. Am. Chem. Soc., 2007, 129, 4908;
(
c) A. Cordova, Catalytic Asymmetric Conjugate Reactions,
Wiley-VCH: Weinheim, 2010; (d) A. Suzuki, Organoboranes in
syntheses, ACS symposium series 783, American Chemical
Society, Washington, 2001; (e) C. E. Tucker, J. Davidson, P.
Knochel, J. Org. Chem., 1992, 57, 3482.
and cooled to room temperature, the solid product was
filtered, and then rinsed with water and ethanol three times,
and dried at room temperature.
2
(a) X. He and J. F. Hartwig, J. Am. Chem. Soc., 1996,118, 1696;
(
b) R. Crabtree, M. Mingos and I. Ojima, in Comprehensive
4.2 General procedure for the preparation of vinylboronates
CH CH OH (2 mL), the alkyne (0.4 mmol), B Pin (112mg, 0.44
Organometallic Chemistry III, Elsevier, Oxford, 2007; (c) A.
Pelter, K. Smith, H. C. Brown, Borane reagents, Academic
Press, New York, 1988; (d) G. J. Irvine, M. J. G. Lesley, T. B.
Marder, N. C. Norman, C. R. Rice, E. G. Robins, W. R. Roper, G.
3
2
2
2
mmol), sodium methoxide (2.2 mg, 0.04 mmol) and Cu-
CuFe O nanoparticles (0.6 mg, 0.5 mol %) were added to a
2
4
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