Paper
4-Methyl-N-(2-phenylpent-4-en-2-yl)benzenesulfonamide (3r).
Organic & Biomolecular Chemistry
Acknowledgements
1
White solid. H NMR (400 MHz, CDCl3): δ 7.56 (d, J = 8.2 Hz,
2H), 7.28 (dd, J = 7.7, 1.5 Hz, 2H), 7.21–7.12 (m, 5H), 5.54–5.43 We thank the Natural Science Foundation of China (21162013)
(m, 1H), 5.26 (d, J = 4.0 Hz, 1H), 5.10 (dd, J = 13.3, 6.9 Hz, 2H), for financial support, Drs Yong Liang and Lei Jiao for helpful
2.69 (dd, J = 13.7, 7.1 Hz, 1H), 2.53 (dd, J = 13.6, 7.4 Hz, 1H), discussions, and Prof. Xiaoqian Han for assistance with HPLC
2.38 (s, 3H), 1.63 (s, 3H). 13C NMR (100 MHz, CDCl3): δ 143.56, analysis.
142.55, 139.86, 132.60, 129.18, 128.00, 126.85, 125.94, 120.00,
60.60, 47.98, 25.59, 21.38. HRMS (ESI): (M
+
Na)+
C18H21NNaO2S, Calcd 338.1191, found 338.1185. m.p.
83–84 °C.
Notes and references
4-Methyl-N-(3-methyl-4-phenylbut-3-en-2-yl)benzenesulfon-
amide (3x). White solid. H NMR (400 MHz, CDCl3): δ 7.75 (d,
1 (a) D.-G. Yu, B.-J. Li and Z.-J. Shi, Acc. Chem. Res., 2010, 43,
1
1486, and references therein;
(b) B. M. Rosen,
J = 8.2 Hz, 2H), 7.30–7.15 (m, 5H), 7.01 (d, J = 7.4 Hz, 2H), 6.25
(s, 1H), 5.03 (d, J = 7.2 Hz, 1H), 4.10–4.00 (m, 1H), 2.36 (s, 3H),
1.56 (s, 3H), 1.28 (d, J = 6.9 Hz, 3H). 13C NMR (100 MHz,
CDCl3): δ 143.09, 137.87, 137.23, 137.00, 129.40, 128.81,
127.91, 127.29, 126.79, 126.46, 57.26, 21.40, 20.71, 13.12.
HRMS (ESI): (M + Na)+ C18H21NNaO2S, Calcd 338.1191, found
338.1185. m.p. 101–102 °C.
N-(2-Methyl-3-phenylallyl)-4-nitroaniline (3y). Yellow solid.
1H NMR (400 MHz, CDCl3): δ 8.09 (d, J = 9.2 Hz, 2H), 7.35–7.32
(m, 2H), 7.25–7.21 (m, 3H), 6.60 (d, J = 9.2 Hz, 2H), 6.49 (s,
1H), 4.86 (s, 1H), 3.94 (d, J = 5.8 Hz, 2H), 1.92 (s, 3H). 13C NMR
(100 MHz, CDCl3): δ 153.39, 138.22, 137.09, 133.61, 128.80,
128.22, 126.71, 126.55, 126.39, 111.35, 51.44, 16.20. HRMS
(ESI): (M + H)+ C16H17N2O2, Calcd 269.1290, found 269.1285.
m.p. 114–115 °C.
N-(2-Benzylideneoctyl)-4-nitroaniline (3z). Yellow solid.
1H NMR (400 MHz, CDCl3): δ 8.10 (d, J = 9.1 Hz, 2H), 7.33 (t,
J = 7.4 Hz, 2H), 7.20 (d, J = 7.5 Hz, 2H), 6.59 (d, J = 9.1 Hz, 2H),
6.48 (s, 1H), 4.77 (s, 1H), 3.95 (d, J = 5.7 Hz, 2H), 2.31–2.26 (m,
2H), 1.29 (dd, J = 17.0, 7.8 Hz, 8H), 0.87 (t, J = 6.5 Hz, 3H). 13C
NMR (100 MHz, CDCl3): δ 153.25, 138.10, 128.46, 128.16,
126.57, 126.29, 111.25, 49.14, 31.46, 29.52, 29.34, 28.30, 22.50,
13.96. HRMS (ESI): (M + H)+ C21H27N2O2, Calcd 339.2073,
found 339.2067. m.p. 74–75 °C.
K. W. Quasdorf, D. A. Wilson, N. Zhang, A. M. Resmerita,
N. K. Garg and V. Percec, Chem. Rev., 2011, 111, 1346.
2 (a) J. W. Dankwardt, Angew. Chem., Int. Ed., 2004, 43, 2428;
(b) S. Ueno, E. Mizushima, N. Chatani and F. Kakiuchi,
J. Am. Chem. Soc., 2006, 128, 16516; (c) B.-T. Guan,
S.-K. Xiang, T. Wu, Z.-P. Sun, B.-Q. Wang, K.-Q. Zhao and
Z.-J. Shi, Chem. Commun., 2008, 1437; (d) T. Shimasaki,
Y. Konno, M. Tobisu and N. Chatani, Org. Lett., 2009, 11,
4890; (e) J. M. Nichols, L. M. Bishop, R. G. Bergman and
J. A. Ellman, J. Am. Chem. Soc., 2010, 132, 12554;
(f) A. Iijima and H. Amii, Tetrahedron Lett., 2008, 49, 6013;
(g) G. A. Molander and F. Beaumard, Org. Lett., 2010, 12,
4022; (h) B.-J. Li, D.-G. Yu, C.-L. Sun and Z.-J. Shi,
Chem.–Eur. J., 2011, 17, 1728.
3 (a) B.-T. Guan, S.-K. Xiang, B.-Q. Wang, Z.-P. Sun, Y. Wang,
K.-Q. Zhao and Z.-J. Shi, J. Am. Chem. Soc., 2008, 130, 3268;
(b) H. T. Dao, U. Schneider and S. Kobayashi, Chem.
Commun., 2011, 47, 692; (c) C. Chen and S. H. Hong, Org.
Lett., 2012, 14, 2992; (d) S. Son and F. D. Toste, Angew.
Chem., Int. Ed., 2010, 49, 3791; (e) R. E. Mulvey, V. L. Blair,
W. Clegg, A. R. Kennedy, J. Klett and L. Russo, Nat. Chem.,
2010, 2, 588; (f) X. W. Guo, S. G. Pan, J. H. Liu and Z. P. Li,
J. Org. Chem., 2009, 74, 8848; (g) B.-Q. Wang, S.-K. Xiang,
Z.-P. Sun, B.-T. Guan, P. Hu, K.-Q. Zhao and Z.-J. Shi, Tetra-
hedron Lett., 2008, 49, 4310; (h) B. L. H. Taylor, E. C. Swift,
J. D. Waetzig and E. R. Jarvo, J. Am. Chem. Soc., 2011, 133,
389; (i) X. Han, Y. Zhang and J. Wu, J. Am. Chem. Soc., 2010,
132, 4104.
4 (a) M. R. Netherton and G. C. Fu, Angew. Chem., Int. Ed.,
2002, 41, 3910; (b) S. P. Y. Cutulic, N. J. Findlay, S. Z. Zhou,
E. J. T. Chrystal and J. A. Murphy, J. Org. Chem., 2009, 74,
8713.
5 (a) P. Rubenbauer and T. Bach, Adv. Synth. Catal., 2008,
350, 1125; (b) D. A. Powell and G. Pelletier, Tetrahedron
Lett., 2008, 49, 2498; (c) M. Feuerstein, D. Laurenti,
H. Doucet and M. Santelli, Tetrahedron Lett., 2001, 42,
2313; (d) H.-P. Deng, Y. Wei and M. Shi, Eur. J. Org. Chem.,
2011, 1956.
6 With only a few exceptions, the alcohols that were reported
previously for Lewis and Brønsted acids catalyzed N-alkyl-
ation are limited to secondary benzylic and allylic alcohols,
for the borrowing-hydrogen methodologies, the substrates
are limited to primary benzylic alcohols, see: (a) U. Jana,
S. Maiti and S. Biswas, Tetrahedron Lett., 2008, 49, 858;
N-(1-(Naphthalen-1-yl)propyl)-4-nitroaniline (3nb). 1H NMR
(400 MHz, CDCl3): δ 8.09 (d, J = 8.4 Hz, 1H), 7.91 (t, J = 9.4 Hz,
3H), 7.74 (d, J = 8.1 Hz, 1H), 7.60–7.50 (m, 2H), 7.45 (d, J = 7.1
Hz, 1H), 7.36 (t, J = 7.7 Hz, 1H), 6.40 (d, J = 9.0 Hz, 2H),
5.20–5.13 (m, 2H), 2.17–2.05 (m, 1H), 1.95–1.87 (m, 1H), 1.06
(t, J = 7.4 Hz, 3H). 13C NMR (100 MHz, CDCl3): δ 152.74,
137.98, 137.16, 134.15, 130.78, 129.41, 128.08, 126.50, 126.29,
125.78, 125.61, 122.80, 122.10, 111.86, 55.36, 30.37, 11.11.
HRMS (ESI): (M + H)+ C19H19N2O2, Calcd 307.1447, found
307.1441.
1-(1-Azido-1-phenylmethyl)-2,4-dichlorobenzene
(3je). 1H
NMR (400 MHz, CDCl3): δ 7.44 (d, J = 8.4 Hz, 1H), 7.38 (d, J =
1.8 Hz, 1H), 7.36–7.26 (m, 6H), 6.09 (s, 1H). 13C NMR
(100 MHz, CDCl3): δ 137.68, 135.95, 134.43, 133.65, 129.62,
129.56, 128.79, 128.42, 127.51, 64.43.
4-Phenyl-3-methyl-3-buten-2-yl
azide
(3xe). 1H
NMR
(400 MHz, CDCl3): δ 7.35 (t, J = 7.5 Hz, 2H), 7.30–7.22 (m, 3H),
6.51 (s, 1H), 4.16 (q, J = 6.8 Hz, 1H), 1.89 (s, 3H), 1.37 (d, J =
6.8 Hz, 3H). 13C NMR (100 MHz, CDCl3): δ 136.91, 136.73,
129.08, 128.37, 128.19, 127.79, 126.83, 65.47, 18.66, 13.64.
2152 | Org. Biomol. Chem., 2013, 11, 2147–2153
This journal is © The Royal Society of Chemistry 2013