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Ple Da s ae l tdo onn To rt aa nd sj ua s ct t mi o an r sg ins
DOI: 10.1039/C6DT00470A
Journal Name
ARTICLE
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Superflip structure solution program using Charge Flipping 2. (a) P. N. Rylander, Hydrogenation Methods, Academic Press:
3
2
and refined with the ShelXL refinement package using Least
Squares minimization. CCDC number 1451179 contains the
supplementary crystallographic data for this paper. These data
can be obtained free of charge from The Cambridge
Crystallographic Data Centre.
New York, 1985, chapter 8; (b) R. A. W. Johnstone, A. H. Wilby
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4
General Procedure for the Hydrosilylation of Nitroarenes
1
. K. M. Doxsee, M. Fiegel, K. D. Stewart, J. W. Canary, C. B.
In an oven-dried Schlenk flask, complex
1 (0.005 mmol, 5
Knobler and D. J. Cram, J. Am. Chem. Soc., 1987, 109, 3098–
mol%), 2 mmol PhSiH (248µL) and 1 mmol of the appropriate
3
3107.
nitroarene in dry THF (2 mL) were added together. The mixture
o
was stirred for 1 hour in a preheated oil bath at 60 C. The
5. A. Saha and B. C. Ranu, J. Org. Chem. 2008, 73, 6867–6870.
6
. (a) L. Liu, B. Qiao, Z. Chen, J. Zhang and Y. Deng, Chem.
Commun., 2009, 653-655. (b) L. He, L. C. Wang, H. Sun, J. Ni,
Y. Cao, H.-Y. He and K.-N. Fan, Angew. Chem., Int. Ed., 2009,
reaction was monitored by TLC. After consumption of the
starting material, the reaction mixture was opened to the air
and MeOH (1 mL) was added followed by aqueous NaOH (2 M,
48, 9538-9541. (c) J. Huang, L. Yu, L. He, Y.-M. Liu,Y. Cao and
2
mL). The resulting mixture was stirred for 1 h and
K.-N. Fan, Green Chem., 2011, 13, 2672-2677.
subsequently extracted with DCM (3 × 30 mL). The organic
7
.
C. T. Redemann and C. E. Redemann, Org. Synth. Coll., 1955,
phase was concentrated in vacuum, and the purity of the
1
3, 69.
residue was checked by
H NMR spectroscopy. Flash
chromatography (a mixture of EtOAc and petroleum ether was 8. M. Okazaki, Y. Suhara and K. Oda, J. Soc. Organ. Synth.
used as the eluent, and the ratio of EtOAc to petroleum ether
Chem., Jpn., 1956, 14, 504.
was adjusted accordingly) was performed unless the crude 9. D. Setamdideh, B. Khezri and M. Mollapour, Orient. J. Chem.,
product was estimated to be greater than 95% pure.
2011, 27, 991-996.
1
1
1
1
0. S. Park, I. S. Lee and J. Park, Org. Biomol. Chem., 2013, 11,
Procedure for Catalyst Longevity Experiment
3
95-399.
1. P. L. Gkizis, M. Stratakis and I. N. Lykakis, Catal. Commun.,
013, 36, 48-51.
In a Schlenk flask, the complex
1 (5 mol%), phenylsilane (2
2
mmol) and 4-nitrotoluene (1 mmol) were taken and stirred at
2. E. Vasilikogiannaki, C. Gryparis, V. Kotzabasaki, I. N. Lykakis
and M. Stratakis, Adv. Synth. Catal., 2013, 355, 907-911.
3. (a) H. Imai, T. Nishiguchi and K. Fukuzumi, Chem. Lett., 1976,
o
1
60
C. The reaction mixture was monitored by H NMR
spectroscopy by taking aliquots of the reaction mixture after 1
intervals and the reaction was stopped when the
h
6
55; (b) Y. Watanabe, T. Ohta, Y. Tsuji, T. Hiyoshi and Y. Tsuji,
consumption of substrates got complete. Again a fresh batch
of substrates phenylsilane (2 mmol) and 4-nitrotoluene (1
mmol) were added for the next catalytic cycle without adding
any further catalyst into the reaction vessel. This procedure
was repeated for a total of five consecutive catalytic runs.
Bull. Chem. Soc. Jpn., 1984, 57, 2440.
1
1
1
4. M. Mirza-Aghayana, R. Boukherroubb, M. Rahimifarda and M.
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5. K. Junge, B. Wendt, N. Shaikh and M. Beller, Chem. Commun.,
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6. S. Park, I. S. Lee and J. Park, Org. Biomol. Chem., 2013, 11, 395–
99.
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Acknowledgements
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8. H. R. Brinkman, W. H. Miles, M. D. Hilborn and M. C. Smith,
We thank SERB (DST), India (Grant No. SR/S1/IC-25/2012) for
financial support. GVK is thankful to UGC, New Delhi for
research fellowship.
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