5154
L. Zhu et al. / Tetrahedron 67 (2011) 5150e5155
Me), 2.35 (s, 3H, Me). 13C NMR (125 MHz, CDCl3)
d
149.9, 139.1,
3.30 (s, 3H, Me). 13C NMR (125 MHz, CDCl3)
d 160.5, 150.4, 148.8,
138.8, 129.0, 128.5, 126.8, 126.7, 117.5, 113.0, 109.6, 56.6, 38.4, 21.9.
129.7, 129.2, 121.9, 121.6, 112.2, 105.8, 105.2, 55.2, 40.3.
MS (%) (EI) (m/z) 211 (Mþ, 60), 134 (62), 91 (100); HRMS (EI) calcd
for C15H17N: 211.1361; found: 211.1360. IR (neat)
2813, 1601, 1580, 1451, 1353, 1180, 1203, 952, 764, 731, 713,
691 cmꢁ1
n
3025, 2914, 2854,
4.3.34. Compound 7v3h. A pale yellow liquid. 1H NMR (500 MHz,
CDCl3, TMS)
d
8.23 (dd, J¼5.0, 1.0 Hz, 1H, Ar), 7.40 (t, J¼8.0 Hz, 2H,
.
Ar), 7.21e7.27 (m, 4H, Ar), 6.61 (dd, J¼6.5, 5.0 Hz, 1H, Ar), 6.53 (d,
J¼8.5 Hz, 1H, Ar), 3.48 (s, 3H, Me). 13C NMR (125 MHz, CDCl3)
4.3.26. Compound 7n. A pale yellow liquid. 1H NMR (500 MHz,
CDCl3, TMS)
d 158.8, 147.8, 146.8, 136.5, 129.7, 126.3, 125.4, 113.1, 109.2, 38.4.
d
7.38 (d, J¼7.0 Hz, 2H, Ar), 7.32 (t, J¼7.5 Hz, 2H, Ar),
7.25 (t, J¼7.5 Hz, 1H, Ar), 7.14e7.21 (m, 2H, Ar), 7.07 (d, J¼8.0 Hz, 1H,
4.3.35. Compound 7w3h. A pale yellow liquid. 1H NMR (500 MHz,
CDCl3, TMS)
Ar), 6.98 (t, J¼7.5 Hz, 1H, Ar), 4.03 (s, 2H), 2.58 (s, 3H, Me), 2.40 (s,
d
8.30 (d, J¼3.0 Hz, 1H, Ar), 8.12 (d, J¼4.5 Hz, 1H, Ar),
3H, Me). 13C NMR (125 MHz, CDCl3)
d
152.4, 139.1,132.8, 131.1, 128.3,
7.33 (t, J¼8.0 Hz, 2H, Ar), 7.21e7.23 (m, 1H, Ar), 7.13 (dd, J¼8.5,
128.2, 126.9, 126.4, 123.0, 120.0, 60.7, 40.8, 18.4. MS (%) (EI) (m/z):
4.5 Hz, 1H, Ar), 7.06e7.10 (m, 3H, Ar), 3.33 (s, 3H, Me). 13C NMR
211 (Mþ, 41), 134 (38), 120 (53), 91 (100); HRMS (EI) calcd for
(125 MHz, CDCl3)
123.2, 122.4, 40.0.
d 147.9, 145.1, 141.0, 140.5, 129.6, 124.7, 123.4,
C15H17N: 211.1361; found: 211.1357. IR (neat)
2841, 2786, 1598, 1493, 1452, 1360, 1329, 1221, 1171, 1091, 1051,
1029, 943, 763, 721, 696 cmꢁ1
n 3061, 3026, 2947,
.
Acknowledgements
4.3.27. Compound 7o14. A pale yellow liquid. 1H NMR (500 MHz,
CDCl3, TMS)
7.22 (t, J¼7.5 Hz, 2H, Ar), 7.15 (t, J¼7.5 Hz, 3H, Ar), 6.74
Financial support from the start-up fund of Wenzhou University
is greatly acknowledged.
d
(d, J¼7.5 Hz, 2H, Ar), 6.66 (d, J¼7.5 Hz, 2H, Ar), 4.34 (s, 2H), 3.67 (s,
3H, OMe), 2.83 (s, 3H, Me). 13C NMR (125 MHz, CDCl3)
139.3, 128.5, 127.2, 126.9, 114.9, 114.8, 58.1, 55.8, 39.1.
d 152.1, 145.0,
Supplementary data
Supplementary data associated with this article can be found in
clude MOL files and InChiKeys of the most important compounds
described in this article.
4.3.28. Compound 7p. A pale yellow liquid. 1H NMR (500 MHz,
CDCl3, TMS) 7.28e7.31 (m, 2H, Ar), 7.21e7.24 (m, 3H, Ar), 7.10e7.13
d
(m, 1H, Ar), 6.36e6.38 (m, 1H, Ar), 6.27e6.29 (m, 2H, Ar), 4.51 (s,
2H), 3.75 (s, 3H, OMe), 3.00 (s, 3H, Me). 13C NMR (125 MHz, CDCl3)
d
160.7, 151.1, 138.9, 129.8, 128.5, 126.8, 126.7, 105.5, 101.3, 98.9, 56.5,
55.0, 38.5. MS (%) (EI) (m/z): 227 (Mþ, 87), 150 (69), 91 (100); HRMS
(EI) calcd for C15H17NO: 227.1310; found: 227.1307. IR (neat) 2930,
2831, 1610, 1574,1499, 1451, 1370,1353,1245,1202, 1166,1116,1053,
956, 821, 749, 732, 711, 686 cmꢁ1
References and notes
n
1. (a) King, A. O.; Yasuda, N. In Organometallics in Process Chemistry; Larsen, R. D.,
Ed.; Springer: Berlin, 2004; pp 205e246; and references therein; (b) Lawrence,
S. A. Amines, Synthesis Properties, and Application; Cambridge University:
Cambridge, 2004; (c) Belfield, A.; Brown, G. R.; Foubister, A. J. Tetrahedron 1999,
55, 11399e11428; (d) Goodbrand, H. B.; Hu, N.-X. J. Org. Chem. 1999, 64,
670e674; (e) O’Hagan, D. Nat. Prod. Rep. 2000, 17, 435e446; (f) Craig, P. N. In
Comprehensive Medicinal Chemistry; Drayton, C. J., Ed.; Pergamon: New York,
NY, 1991; Vol. 8; (g) Kundu, N. G.; Mahanty, J. S.; Chowdhurry, C.; Dasgupta, S.
K.; Das, B.; Spears, C. P.; Balzarini, J.; De Clercq, E. Eur. J. Med. Chem. 1999, 34,
389e398.
2. (a) Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927e928; (b) Guram,
A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34,
1348e1350; (c) Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609e3612.
3. For some selected examples, please see: (a) Nishiyama, M.; Yamamoto, T.; Koie,
Y. Tetrahedron Lett. 1998, 39, 617e620; (b) Netherton, M. R.; Fu, G. C. Org. Lett.
2001, 3, 4295e4298; (c) Rataboul, F.; Zapf, A.; Jackstell, R.; Harkal, S.; Riermeier,
T.; Monsees, A.; Dingerdissen, U.; Beller, M. Chem.dEur. J. 2004, 10, 2983e2990;
(d) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem.
2000, 65, 1158e1174; (e) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J.
Org. Chem. 2002, 67, 5553e5566; (f) Urgaonkar, S.; Xu, J.-H.; Verkade, J. G. J. Org.
Chem. 2003, 68, 8416e8423; (g) Urganonkar, S.; Verkade, J. G. J. Org. Chem.
2004, 69, 9135e9142; (h) Reddy, C. V.; Kingston, J. V.; Verkade, J. G. J. Org. Chem.
2008, 73, 3047e3062.
.
4.3.29. Compound 7q15. A pale yellow liquid. 1H NMR (500 MHz,
CDCl3, TMS)
8.18 (dd, J¼4.5, 1.0 Hz, 1H, Ar), 7.21e7.30 (m, 6H, Ar),
6.56 (dd, J¼6.5, 5.0 Hz, 1H, Ar), 6.50 (d, J¼8.5 Hz, 1H, Ar), 4.80 (s,
2H), 3.07 (s, 3H, Me). 13C NMR (125 MHz, CDCl3)
158.9, 148.0,
138.7, 137.3, 128.5, 127.0, 126.9, 111.8, 105.7, 53.2, 36.1.
d
d
4.3.30. Compound 7r. A pale yellow liquid. 1H NMR (500 MHz,
CDCl3, TMS)
d
8.16 (d, J¼3.0 Hz, 1H, Ar), 7.96 (dd, J¼5.0, 1.0 Hz,
1H, Ar), 7.32 (t, J¼7.5 Hz, 2H, Ar), 7.26 (t, J¼4.0 Hz, 1H, Ar),
7.19e7.21 (m, 2H, Ar), 7.08e7.10 (m, 1H, Ar), 6.98 (dd, J¼8.0,
1.0 Hz, 1H, Ar), 4.54 (s, 2H), 3.06 (s, 3H, Me). 13C NMR (125 MHz,
CDCl3)
56.1, 38.3. MS (%) (EI) (m/z): 198 (Mþ, 51), 91 (100); HRMS (EI)
calcd for C13H14N2: 198.1157; found: 198.1158. IR (neat) 3023,
2898, 1585, 1493, 1452, 1376, 1348, 1233, 1052, 1004, 946, 933,
726, 708, 694 cmꢁ1
d 145.3, 137.9, 137.8, 134.9, 128.7, 127.1, 126.6, 123.4, 118.6,
n
4. For some selected reviews on NHCs, please see: (a) Herrmann, W. A. Angew.
Chem., Int. Ed. 2002, 41, 1290e1309; (b) Marion, N.; Nolan, S. P. Acc. Chem.
Res. 2008, 41, 1440e1449; (c) Peris, E.; Crabtree, R. H. Coord. Chem. Rev. 2004,
.
€
248, 2239e2246; (d) Herrmann, W. A.; Ofele, K.; Preysing, D. V.; Schneider,
4.3.31. Compound 7s16. A pale yellow liquid. 1H NMR (500 MHz,
CDCl3, TMS) 7.27e7.30 (m, 4H, Ar), 7.03e7.05 (m, 4H, Ar),
6.95e6.99 (m, 2H, Ar), 3.33 (s, 3H, Me). 13C NMR (125 MHz, CDCl3)
149.0, 129.2, 121.2, 120.4, 40.2.
K. S. J. Organomet. Chem. 2003, 687, 229e248; (e) Hahn, F. E.; Jahnke, M. C.
Angew. Chem., Int. Ed. 2008, 47, 3122e3172; (f) Glorius, F. N-Heterocyclic
Carbenes in Transition Metal Catalysis; Springer: Berlin, Germany, 2007; (g)
Nolan, S. P. N-Heterocyclic Carbenes in Synthesis; Wiley-VCH: Weinheim,
d
d
ꢁ
Germany, 2006; (h) Díez-Gonzalez, S.; Nolan, S. P. Coord. Chem. Rev. 2007,
251, 874e883.
4.3.32. Compound 7t3h. A pale yellow liquid. 1H NMR (500 MHz,
CDCl3, TMS)
7.17e7.21 (m, 2H, Ar), 7.09 (dd, J¼6.5, 2.0 Hz, 2H, Ar),
5. (a) Li, J.-Y.; Cui, M.-J.; Yu, A.-J.; Wu, Y.-J. J. Organomet. Chem. 2007, 692,
3732e3742; (b) Gooßen, L. J.; Paetzold, J.; Briel, O.; Rivas-Nass, A.; Karch, R.;
Kayser, B. Synlett 2005, 275e278; (c) Viciu, M. S.; Kissling, R. M.; Stevens, E. D.;
Nolan, S. P. Org. Lett. 2002, 4, 2229e2231; (d) Viciu, M. S.; Kelly, R. A., III; Ste-
vens, E. D.; Naud, F.; Studer, M.; Nolan, S. P. Org. Lett. 2003, 5, 1479e1482; (e) Jin,
Z.; Guo, S.-X.; Gu, X.-P.; Qiu, L.-L.; Song, H.-B.; Fang, J.-X. Adv. Synth. Catal. 2009,
351, 1575e1585; (f) Organ, M. G.; Abdel-Hadi, M.; Avola, S.; Dubovyk, I.; Hadei,
N.; Kantchev, E. A. B.; O’Brien, C. J.; Sayah, M.; Valente, C. Chem.dEur. J. 2008, 14,
2443e2452; (g) Viciu, M. S.; Navarro, O.; Germaneau, R. F.; Kelly, R. A., III;
Sommer, W.; Marion, N.; Stevens, E. D.; Cavallo, L.; Nolan, S. P. Organometallics
2004, 23, 1629e1635; (h) Jin, Z.; Qiu, L.-L.; Li, Y.-Q.; Song, H.-B.; Fang, J.-X.
Organometallics 2010, 29, 6578e6586; (i) Broggi, J.; Clavier, H.; Nolan, S. P.
Organometallics 2008, 27, 5525e5531.
d
6.88 (dd, J¼6.5, 2.0 Hz, 2H, Ar), 6.78e6.79 (m, 3H, Ar), 3.80 (s, 3H,
OMe), 3.25 (s, 3H, Me). 13C NMR (125 MHz, CDCl3)
142.2, 128.9, 126.2, 118.3, 115.7, 114.7, 55.5, 40.4.
d 156.2, 149.7,
4.3.33. Compound 7u3h. A pale yellow liquid. 1H NMR (500 MHz,
CDCl3, TMS)
d
7.29 (t, J¼8.0 Hz, 2H, Ar), 7.16 (t, J¼8.0 Hz, 1H, Ar),
7.06e7.07 (m, 2H, Ar), 6.99 (t, J¼7.5 Hz, 1H, Ar), 6.57e6.59 (m, 1H,
Ar), 6.53e6.54 (m, 1H, Ar), 6.47e6.50 (m, 1H, Ar), 3.75 (s, 3H, OMe),