Communication
RSC Advances
¼
133.1, 131.7, 128.4, 118.6, 111.9; HRMS (EI): calcd for C
03.0422, found 103.0419.
7
H
5
N
3-Cyanopyridine (2l). IR (neat): n ¼ 3070, 2230, 1615, 1556,
1
6a
1
1475, 1290; H NMR (400 MHz, CDCl ); d ¼ 8.89 (d, 2H, J ¼ 6.0
3
13
4
-Methylbenzonitrile (2b). IR (neat): n ¼ 2922, 2234, 1601, Hz), 7.63 (d, 1H, J ¼ 6.0 Hz), 7.31 (s, 1H); C NMR (100 MHz,
ꢂ1
1
6a
6a
1
7
453, 1387, 857, 672 cm ; H NMR (400 MHz, CDCl ); d ¼ CDCl ); d ¼ 152.6, 152.3, 139.5, 123.6, 116.4, 110.2; HRMS (EI):
3
3
1
3
.43 (d, 2H, J ¼ 8.4 Hz), 7.29 (d, 2H, J ¼ 8.4 Hz), 2.33 (s, 3H);
C
6 4 2
calcd for C H N 104.1094, found 104.1092.
6a
20c
NMR (100 MHz, CDCl
3
); d ¼ 142.1, 131.2, 129.0, 117.9, 108.2,
Benzofuran-2-carbonitrile (2m). IR (neat): n ¼ 2228, 1614,
ꢂ1 1
21.0; HRMS (EI): calcd for C
8
2
H
7
0c
N 117.0578, found 117.0580.
1555, 1443, 1184, 825, 750, 418 cm
; H NMR (400 MHz,
4
-Methoxybenzonitrile (2c). IR (neat): n ¼ 2925, 2220, 1610, CDCl ); d ¼ 7.67 (d, J ¼ 8.4 Hz, 1H), 7.58–7.47 (m, 2H), 7.46 (s,
3
ꢂ1
1
13
1509, 1463, 1259, 1173, 1025, 830 cm ; H NMR (400 MHz, 1H), 7.40–7.33 (m, 1H); C NMR (100 MHz, CDCl
3
); d ¼ 155.7,
CDCl ); d ¼ 7.60 (d, 2H, J ¼ 9.0 Hz), 6.95 (d, 2H, J ¼ 9.0 Hz), 3.85 128.5, 127.2, 125.6, 124.4, 122.4, 118.5, 112.0, 111.8; HRMS (EI):
3
1
3
(
1
s, 3H); C NMR (100 MHz, CDCl ); d ¼ 162.9, 134.8, 119.0, calcd for C H NO 143.0371, found 143.0372.
3
9
5
14.5, 104.1, 55.2; HRMS (EI): calcd for C H NO 133.0528,
8
7
found 133.0531.
1
6
Acknowledgements
-Hydroxy-3-methoxybenzonitrile (2d). IR (KBr): n ¼ 3365,
ꢂ1 1
4
3
226, 2231, 1605, 1525, 1369, 1283 cm ; H NMR (400 MHz,
CDCl
); d ¼ 7.20 (d, 1H, J ¼ 8.0 Hz), 7.10 (s, 1H), 6.92 (d, 1H, J ¼
3
.0 Hz), 6.44 (brs, 1H), 3.91 (s, 3H); C NMR (100 MHz, CDCl );
We sincerely thank the SAIF, Punjab University, Chandigarh, for
providing spectra. V.P.S. is grateful to the Department of
Science and Technology (DST) Govt. of India, for the award of a
DST-Inspire Faculty position (Ref. IFA-11CH-08) and nancial
support and A.K.Y. is grateful to the CSIR, New Delhi, for the
award of a Senior Research Fellowship.
3
1
3
8
d ¼ 148.9, 145.9, 126.7, 119.7, 115.6, 115.0, 103.0, 55.6; HRMS
(
EI): calcd for C H NO 149.0476, found 149.0475.
8 7 2
2
-Aminobenzonitrile (2e). IR (KBr): n ¼ 3450, 3370, 2240,
ꢂ1 1
6a
1
615, 1590, 1260 cm ; H NMR (400 MHz, CDCl
3
); d ¼ 7.40–
1
3
7
.25 (d, 2H), 6.7 (t, 2H), 4.5 (brs, 2H, J ¼ 4.0 Hz, J ¼ 1.5 Hz);
C
6
a
NMR (100 MHz, CDCl
3
); d ¼ 148.3, 132.9, 131.2, 117.1, 116.3,
118.0531, found
Notes and references
1
1
14.0, 95.1; HRMS (EI): calcd for C
18.0535.
7 6 2
H N
1 For leading reviews, see: (a) X. Lang, X. Chen and J. Zhao,
Chem. Soc. Rev., 2014, 43, 473; (b) D. Ravelli, M. Fagnoni
and A. Albini, Chem. Soc. Rev., 2013, 42, 97; (c) J. Hu,
J. Wang, T. H. Nguyen and N. Zheng, Beilstein J. Org.
Chem., 2013, 9, 1977; (d) C. K. Prier, D. A. Rankic and
D. W. C. MacMillan, Chem. Rev., 2013, 113, 5322; (e)
D. Ravelli and M. Fagnoni, ChemCatChem, 2012, 4, 169; (f)
J. Xuan and W.-J. Xiao, Angew. Chem., Int. Ed., 2012, 51,
6828; (g) J. M. R. Narayanam and C. R. J. Stephenson,
Chem. Soc. Rev., 2011, 40, 102; (h) F. Teply, Collect. Czech.
Chem. Commun., 2011, 76, 859; (i) T. P. Yoon, M. A. Ischay
and J. N. Du, Nat. Chem., 2010, 2, 527; (j) K. Zeitler, Angew.
Chem., Int. Ed., 2009, 48, 9785.
17
4
-Bromobenzonitrile (2f). IR (KBr): n ¼ 3100–2845, 2241,
ꢂ1 1
1
593, 1448, 1259, 1041, 832, 670 cm ; H NMR (400 MHz,
17
13
CDCl3); d ¼ 7.61 (dd, 4H, J ¼ 4.0 Hz, J ¼ 1.5 Hz); C NMR
(
(
100 MHz, CDCl
EI): calcd for C
3
); d ¼ 137.9, 132.0, 125.7, 115.7, 108.5; HRMS
4
H BrN 180.9527, found 180.9529.
7
17
4
-Nitrobenzonitrile (2g). IR (KBr): n ¼ 3090, 2965, 2846, 2232,
ꢂ1 1
1
595, 1541, 1405, 1337, 1081, 781 cm ; H NMR (400 MHz,
CDCl
17
13
3
); d ¼ 8.36 (d, 2H, J ¼ 8.5 Hz), 7.91 (d, 2H, J ¼ 8.5 Hz);
C
6a
NMR (100 MHz, CDCl ); d ¼ 149.1, 132.2, 123.5, 117.2, 115.8;
3
HRMS (EI): calcd for C H N O 148.0273, found 148.0270.
7
4
2
2
0c
2
3
-Methoxybenzonitrile (2h). IR (neat): n ¼ 2230, 1585, 1485,
ꢂ1
1
14
1
430, 1264, 1042, 788, 680 cm ; H NMR (400 MHz, CDCl
3
);
d
¼
7.41–7.33 (m, 1H), 7.28–7.22 (m, 1H), 7.16–7.11 (m, 2H), 3.85
2 (a) D. A. Nicewicz and D. W. C. MacMillan, Science, 2008, 322,
77; (b) M. A. Ischay, M. E. Anzovino, J. Du and T. P. Yoon,
J. Am. Chem. Soc., 2008, 130, 12886.
1
3
(
s, 3H); C NMR (100 MHz, CDCl
3
); d ¼ 159.5, 130.0, 124.6,
1
1
19.3, 118.5, 116.9, 113.0, 55.3; HRMS (EI): calcd for C
33.0528, found 133.0526.
,5-Dimethyl benzonitrile (2i). IR (neat): n ¼ 2925, 2230,
8 7
H
NO
3 (a) A. K. Yadav, V. P. Srivastava and L. D. S. Yadav, New
J. Chem., 2013, 37, 4119; (b) V. P. Srivastava, A. K. Yadav
and L. D. S. Yadav, Synlett, 2013, 24, 465; (c) J. Zhang,
L. Wang, Q. Liu, Z. Yang and Y. Huang, Chem. Commun.,
2013, 49, 11662; (d) M. Majek and A. J. von Wanglin, Chem.
Commun., 2013, 49, 5507; (e) D. P. Hari, P. Schroll and
B. K ¨o nig, J. Am. Chem. Soc., 2012, 134, 2958; (f) D. P. Hari,
T. Hering and B. K ¨o nig, Org. Lett., 2012, 14, 5334; (g)
Y.-Q. Zou, J.-R. Chen, X.-P. Liu, L.-Q. Lu, R. L. Davis,
K. A. Jørgensen and W.-J. Xiao, Angew. Chem., Int. Ed.,
2012, 51, 784; (h) K. Fidaly, C. Ceballos, A. Falgui `e res,
M. S.-I. Veitia, A. Guy and C. Ferroud, Green Chem., 2012,
14, 1293; (i) M. Neumann, S. F u¨ ldner, B. K ¨o nig and
K. Zeitler, Angew. Chem., Int. Ed., 2011, 50, 951; (j)
D. P. Hari and B. K ¨o nig, Org. Lett., 2011, 13, 3852.
2
0c
3
ꢂ1
1
1
605, 1455, 1376, 854, 680 cm ; H NMR (400 MHz, CDCl ); d ¼
3
13
7.26 (s, 2H), 7.20 (s, 1H), 2.34 (s, 6H); C NMR (100 MHz,
15
CDCl
3
); d ¼ 138.8, 134.7, 129.5, 119.0, 111.7, 20.8; HRMS (EI):
N 131.0735, found 131.0733.
calcd for C
Phenylacetonitrile (2j). IR (neat): n ¼ 3088, 2958, 2840, 2228,
16
9 9
H
17
ꢂ1
1
3
1605, 1560, 1435, 1264, 968 cm ; H NMR (400 MHz, CDCl );
1
3
6a
d ¼ 7.35 (brs, 5H), 3.74 (s, 2H); C NMR (100 MHz, CDCl
29.9, 129.0, 128.0, 127.5, 117.5, 123.4; HRMS (EI): calcd for
C H N 117.0478, found 117.0480.
3
); d ¼
1
8
7
17
Cinnamonitrile (2k). IR (neat): n ¼ 3082, 2965, 2845, 2234,
ꢂ1
1
1606, 1587, 1435, 1270, 1035, 865, 768 cm ; H NMR (400 MHz,
17
CDCl
3
); d ¼ 7.31–7.62 (m, 5H); 6.01 (d, 1H, J ¼ 17.5 Hz), 5.84 (d,
13
20a
1
1
1
H, J ¼ 17.5 Hz); C NMR (100 MHz, CDCl
3
); d ¼ 150.5, 132.9,
30.9, 128.1, 127.0, 119.1, 95.7; HRMS (EI): calcd for C
29.0578, found 129.0576.
9
H
7
N
4 C. Dai, J. M. R. Narayanam and C. R. J. Stephenson, Nat.
Chem., 2011, 3, 140.
This journal is © The Royal Society of Chemistry 2014
RSC Adv., 2014, 4, 4181–4186 | 4185