10.1002/ejoc.201900831
European Journal of Organic Chemistry
FULL PAPER
4.34 (s, 5H); 13C NMR (100 MHz, CDCl3): δ = 120.2, 71.7, 70.7, 70.6,
51.9; MS (EI, 70 eV): m/z = 211.0 [M]+.
δ = 7.41-7.31 (m, 5H), 3.76 (s, 2H); 13C NMR (100 MHz, CDCl3): δ =
129.8, 129.1, 128.1, 127.9, 117.9, 23.6.; MS (EI, 70 eV): m/z = 117.1 [M]+.
Furan-2-carbonitrile (2y).[8k] Purification by column chromatography on
silica gel (n-pentane/dichloromethane = 10/1, v/v) afforded 2y as a light
yellow liquid (30.2 mg, 0.32 mmol, 65%); 1H NMR (400 MHz, CDCl3): δ =
7.61 (dd, J = 1.6 Hz, 0.4 Hz, 1H), 7.13 (dd, J = 3.6 Hz, 0.8 Hz, 1H), 6.56
(dd, J = 3.6 Hz, 2.0 Hz, 1H); 13C NMR (100 MHz, CDCl3): δ = 147.5,
126.2, 122.1, 111.5; MS (EI, 70 eV): m/z = 93.0 [M]+.
Acknowledgments
We gratefully acknowledge the National Natural Science
Foundation of China (Nos. 21871186, 21572175, and
J1103315/J0104) for financial support..
Thiophene-2-carbonitrile
(2z).[10e]
Purification
by
column
chromatography on silica gel (n-pentane/dichloromethane = 10/1, v/v)
afforded 2z as a light yellow liquid (38.7 mg, 0.36 mmol, 71%); H NMR
(400 MHz, CDCl3): δ = 7.65-7.64 (m, 1H), 7.62-7.61 (m, 1H), 7.14 (dd, J
= 5.2 Hz, 3.6 Hz, 1H); 13C NMR (100 MHz, CDCl3): δ = 137.4, 132.6,
127.6, 114.2, 110.0; MS (EI, 70 eV): m/z = 109.0 [M]+.
Keywords: Nitriles • Oxime esters • Iron • Co-Catalysis •
1
Synthetic methods
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Picolinonitrile (2aa).[10e] Purification by column chromatography on silica
gel (n-pentane/dichloromethane = 10/1, v/v) afforded 2aa as a yellow
1
liquid (45.2 mg, 0.43 mmol, 87%); H NMR (400 MHz, CDCl3): δ = 8.74
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(d, J = 4.8 Hz, 1H), 7.87 (td, J = 8.0 Hz, 1.6 Hz, 1H), 7.72 (d, J = 8.0 Hz,
1H), 7.57-7.53 (m, 1H); 13C NMR (100 MHz, CDCl3): δ = 151.2, 137.1,
134.1, 128.6, 126.9, 117.2; MS (EI, 70 eV): m/z = 104.0 [M]+.
Cinnamonitrile (2ab).[12e] Purification by column chromatography on
silica gel (n-pentane/dichloromethane = 10/1, v/v) afforded 2ab as a
colorless liquid (61.3 mg, 0.48 mmol, 95%); 1H NMR (400 MHz, CDCl3): δ
= 7.47-7.39 (m, 6H), 5.88 (d, J = 16.8 Hz, 1H); 13C NMR (100 MHz,
CDCl3): δ = 150.6, 133.6, 131.2, 129.1, 127.4, 118.2, 96.4; MS (EI, 70
eV): m/z = 129.0 [M]+.
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3-(4-Bromophenyl)acrylonitrile (2ac).[3f] Purification by column
chromatography on silica gel (petroleum ether/dichloromethane = 10/1,
v/v) afforded 2ac as a white solid (101.4 mg, 0.49 mmol, 98%); m.p. =
116-118 oC; 1H NMR (400 MHz, CDCl3): δ = 7.56-7.54 (m, 2H), 7.36-
7.31 (m, 3H), 5.88 (d, J = 16.8 Hz, 1H); 13C NMR (100 MHz, CDCl3): δ =
149.3, 132.4, 128.7, 125.7, 117.9, 97.0; MS (EI, 70 eV): m/z = 207.0 [M]+.
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2-Methyl-3-phenylacrylonitrile (2ad).[12f] Purification by column
chromatography on silica gel (petroleum ether/dichloromethane = 10/1,
v/v) afforded 2ad as a yellow liquid (68.0 mg, 0.48 mmol, 95%); 1H NMR
(400 MHz,CDCl3): δ = 7.44-7.32 (m, 5H), 7.22 (s, 1H), 2.15 (d, J = 1.2Hz,
3H); 13C NMR (100 MHz, CDCl3): δ = 144.5, 134.1, 129.3, 129.3, 128.7,
121.3, 109.6, 16.8; MS (EI, 70 eV): m/z = 143.1 [M]+.
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2-Phenylpropanenitrile (2ae).[13f] Purification by column chromatography
on silica gel (petroleum ether/dichloromethane = 10/1, v/v) afforded 2ae
as a colorless liquid (63.6 mg, 0.49 mmol, 97%); 1H NMR (400 MHz,
CDCl3): δ = 7.41-7.30 (m, 5H), 3.90 (q, J = 7.2 Hz, 1H) , 1.64 (d, J = 7.2
Hz, 3H); 13C NMR (100 MHz, CDCl3): δ = 137.1, 129.2, 128.1, 126.7,
121.6, 31.3, 21.5; MS (EI, 70 eV): m/z = 131.1 [M]+.
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J.-H. Xu, Q. Jiang, C.-C. Guo, J. Org. Chem. 2013, 78, 11881-11886.
D.-W. Gao, E. V. Vinogradova, S. K. Nimmagadda, J. M. Medina, Y.
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Liu, Z. Cao, Org. Biomol. Chem. 2013, 11, 3349-3354; g) J. Kim, S. S.
Stahl, ACS Catal. 2013, 3, 1652-1656; h) M. Varyani, P. K. Khatri, S. L.
Jain, Tetrahedron Lett. 2016, 57, 723-727; i) R. V. Jagadeesh, H.
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M. Rizzi, N. K. Szymczak, J. Am. Chem. Soc. 2013, 135, 16352-16355;
k) I. Dutta, S. Yadav, A. Sarbajna, S. De, M. Hölscher, W. Leitner, J. K.
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1-Cyanoadamantane (2af).[12e] Purification by column chromatography
on silica gel (petroleum ether/dichloromethane = 20/1, v/v) afforded 2af
as a colorless solid (79.7 mg, 0.49 mmol, 99%); m.p. = 185-187 oC; 1H
NMR (400 MHz, CDCl3): δ = 2.04 (br, 9H), 1.74 (t, J = 14.0 Hz, 6H); 13
C
NMR (100 MHz, CDCl3): δ = 125.3, 39.9, 35.7, 30.2, 27.1; MS (EI, 70 eV):
m/z = 161.1 [M]+.
2-Phenylacetonitrile (2ag).[11c] Purification by column chromatography
on silica gel (petroleum ether/dichloromethane = 20/1, v/v) afforded 2ag
as a yellow liquid (51.2 mg, 0.44 mmol, 87%); 1H NMR (400 MHz, CDCl3):
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