Communications
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3-Nitroacetophenone (2d): H NMR (400 MHz, CDCl3) d=8.77–8.76
11-Nitroundecan-2-one (5h): 1H NMR (400 MHz, CDCl3) d=4.37 (t,
J=7.1 Hz, 2H), 2.41 (t, J=7.4 Hz, 2H), 2.13 (s, 3H), 1.99 (quint., J=
7.2 Hz, 2H), 1.61–1.52 (m, 2H), 1.38–1.21 ppm (m, 10H); 13C NMR
(100 MHz, CDCl3) d=209.5, 75.9, 43.9, 31.1, 29.9, 29.4, 29.2, 28.9,
27.6, 26.4, 23.9 ppm.
(m, 1H), 8.42 (d, J=8.0 Hz, 1H), 8.28 (d, J=8.0 Hz, 1H), 7.69 (t, J=
8.0 Hz, 1H), 2.69 ppm (s, 3H); 13C NMR (100 MHz, CDCl3) d=195.8,
148.4, 138.4, 133.9, 130.0, 127.6, 123.4, 26.6 ppm.
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4-(tert-Butyl)acetophenone (2e): H NMR (400 MHz, CDCl3) d=7.90
(d, J=8.4 Hz, 2H), 7.48 (d, J=8.4 Hz, 2H), 2.59 (s, 3H), 1.35 ppm (s,
9H); 13C NMR (100 MHz, CDCl3) d=197.8, 156.8, 134.6, 128.2, 125.4,
35.1, 31.0, 26.5 ppm.
11-Iodoundecan-2-one (5i): 1H NMR (400 MHz, CDCl3) d=3.18 (t,
J=7.0 Hz, 2H), 2.41 (t, J=7.4 Hz, 2H), 2.13 (s, 3H), 1.81 (quint., J=
7.2 Hz, 2H), 1.59–1.54 (m, 2H), 1.39–1.22 ppm (m, 10H); 13C NMR
(100 MHz, CDCl3) d=209.2, 43.7, 33.5, 33.0, 30.4, 29.8, 29.2, 29.1,
29.0, 28.4, 23.7 ppm.
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4-(Chloromethyl)benzaldehyde (3b): H NMR (400 MHz, CDCl3) d=
10.0 (s, 1H), 7.88 (d, J=8.2 Hz, 2H), 7.56 (d, J=8.2 Hz, 2H),
4.63 ppm (s, 2H).
4-Chlorobenzaldehyde (3c): 1H NMR (400 MHz, CDCl3) d=9.98 (s,
1H), 7.83 (dt, J=8.6 Hz, J=2.0 Hz, 2H), 7.51 ppm (dt, J=8.6 Hz, J=
1.7 Hz, 2H); 13C NMR (100 MHz, CDCl3) d=191.1, 141.2, 134.9,
129.7, 129.1 ppm.
Recycling experiment
A typical oxidation reaction of styrene was set up as above starting
from styrene (0.1 mmol), CuCl (5 mol%), and PdCNT (0.56 mol%) in
THF/H2O (4:1, 0.5 mL). The mixture was stirred at room tempera-
ture under an oxygen atmosphere for 24 h. The catalyst was recov-
ered by centrifugation, and the supernatant was worked up as
above. The recovered catalyst was washed with water and reused
in a subsequent oxidation reaction of styrene with added CuCl.
3-Nitrobenzaldehyde (3d): 1H NMR (400 MHz, CDCl3) d=10.13 (s,
1H), 8.73 (t, J=1.6 Hz, 1H), 8.49 (dd, J=7.8 Hz, J=1.6 Hz, 1H), 8.24
(dd, J=7.8 Hz, J=1.6 Hz, 1H), 7.77 ppm (t, J=7.8 Hz, 1H); 13C NMR
(100 MHz, CDCl3) d=189.6, 148.7, 137.3, 134.5, 130.3, 128.5,
124.5 ppm.
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4-tert-Butylbenzaldehyde (3e): H NMR (400 MHz, CDCl3) d=9.99 (s,
Acknowledgements
1H), 7.82 (d, J=8.4 Hz, 2H), 7.55 (d, J=8.4 Hz, 2H), 1.36 ppm (s,
9H); 13C NMR (100 MHz, CDCl3) d=192.0, 158.4, 134.0, 129.6, 125.9,
35.3, 31.0 ppm.
Support from the Indo-French Centre for the Promotion of Ad-
vanced Research (IFCPAR)/Centre Franco-Indien pour la Promo-
tion de la Recherche AvancØe (CEFIPRA) is gratefully acknowl-
edged (Project no. 4705-1). S.D. thanks the Department of Science
and Technology (Government of India) and the Science & Tech-
nology Department (French Embassy in India) for the award of
a Raman-Charpak fellowship. The TEM-team platform (CEA,
iBiTec-S) is acknowledged for help with TEM images. The “Service
de Chimie Bioorganique et de Marquage” belongs to the Labora-
tory of Excellence in Research on Medication and Innovative
Therapeutics (ANR-10-LABX-0033-LERMIT).
2-Tetradecanone (5a): 1H NMR (400 MHz, CDCl3) d=2.41 (t, J=
7.5 Hz, 2H), 2.13 (s, 3H), 1.55–1.60 (m, 2H), 1.20–1.32 (m, 18H),
0.87 ppm (t, J=8.6 Hz, 3H); 13C NMR (100 MHz, CDCl3) d=209.7,
44.0, 32.1, 30.4, 30.0, 29.8, 29.8, 29.7, 29.6, 29.5, 29.4, 24.1, 22.9,
14.3 ppm.
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Methyl 10-oxoundecanoate (5b): H NMR (400 MHz, CDCl3) d=3.64
(s, 3H), 2.39 (t, J=7.4 Hz, 2H), 2.27 (t, J=7.4 Hz, 2H), 2.11 (s, 3H),
1.61–1.51 (m, 4H), 1.29–1.22 ppm (m, 8H); 13C NMR (100 MHz,
CDCl3) d=209.5, 174.5, 51.6, 43.9, 34.2, 30.0, 29.3, 29.2 (3C), 25.0,
23.9 ppm.
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10-Oxoundecanoic acid (5c): H NMR (500 MHz, CDCl3) d=2.41 (t,
Keywords: heterogeneous catalysis · olefins · nanoparticles ·
nanotubes · oxidation
J=7.4 Hz, 2H), 2.36 (t, J=7.4 Hz, 2H), 2.13 (s, 3H), 1.64–1.54 (m,
4H), 1.31–1.24 ppm (m, 8H); 13C NMR (125 MHz, CDCl3) d=209.6,
178.7, 43.9, 30.0, 29.9, 29.3, 29.2 (2C), 29.1, 24.8, 24.0 ppm.
[1] a) J. Tsuji, Palladium Reagents and Catalysts Innovations in Organic Syn-
thesis; Wiley, New York, 1998; b) Metal-Catalyzed Cross-Coupling Reac-
tions (Eds.: F. Diederich, P. J. Stang), Wiley, New York, 1998, pp. 339–
[2] a) R. M. Trend, Y. K. Ramtohul, E. M. Ferreira, B. M. Stoltz, Angew. Chem.
[3] a) T. Mitsudome, T. Umetani, N. Nosaka, K. Mori, T. Mizugaki, K. Ebitani,
10-Oxoundecanal (5d): 1H NMR (500 MHz, CDCl3) d=9.76 (t, J=
1.8 Hz, 1H), 2.43–2.39 (m, 4H), 2.13 (s, 3H), 1.65–1.54 (m, 4H),
1.33–1.24 ppm (m, 8H); 13C NMR (125 MHz, CDCl3) d=209.5, 203.1,
44.0, 43.9, 30.0, 29.3 (2C), 29.2 (2C), 23.9, 22.2 ppm.
11-Hydroxyundecan-2-one (5e): 1H NMR (500 MHz, CDCl3) d=3.62
(t, J=6.6 Hz, 2H), 2.40 (t, J=7.5 Hz, 2H), 2.12 (s, 3H), 1.74 (br s,
1H), 1.56–1.51 (m, 4H), 1.37–1.22 ppm (m, 10H); 13C NMR
(125 MHz, CDCl3) d=209.7, 63.2, 44.0, 32.9, 30.1, 29.6, 29.5, 29.5,
29.3, 25.9, 25.0 ppm.
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11-Bromoundecan-2-one (5 f): H NMR (400 MHz, CDCl3) d=3.40 (t,
J=6.9 Hz, 2H), 2.41 (t, J=7.4 Hz, 2H), 2.13 (s, 3H), 1.84 (quint., J=
7.2 Hz, 2H), 1.60–1.54 (m, 2H), 1.44–1.38 (m, 2H), 1.32–1.22 ppm
(m, 8H); 13C NMR (100 MHz, CDCl3) d=209.6, 44.0, 34.2, 33.0, 30.1,
29.4 (2C), 29.3, 28.9, 28.3, 24.0 ppm.
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11-Azidoundecan-2-one (5g): H NMR (400 MHz, CDCl3) d=3.24 (t,
J=7.0 Hz, 2H), 2.41 (t, J=7.4 Hz, 2H), 2.13 (s, 3H), 1.62–1.54 (m,
4H); 1.38–1.25 ppm (m, 10H); 13C NMR (100 MHz, CDCl3) d=209.6,
51.6, 43.9, 30.0, 29.4 (2C), 29.3, 29.2, 29.0, 26.8, 24.0 ppm.
ChemCatChem 2015, 7, 2318 – 2322
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