788
Can. J. Chem. Vol. 90, 2012
1
3
.65–1.58 (m, 2H), 1.53–1.48 (m, 2H), 0.98 (t, J = 7.1 Hz,
Berlin, 2002; (e) Hegedus, L. S. In Organometallics in
Synthesis; Schlosser, M., Ed.; Wiley: Chichester, 2002; p
H).
1
123; (f) Negishi, E., Ed.; Handbook of Organopalladium
1
-(1-Hexynyl)-4-methoxybenzene (Table 2, entry 10)
Chemistry for Organic Synthesis; Wiley-Interscience: New
York, 2002; (g) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed.
2002, 41 (22), 4176. doi:10.1002/1521-3773(20021115)
25 1
Oil. H NMR (CDCl , 300 MHz) d: 7.34 (d, J = 8.8 Hz,
3
2
7
H), 6.81 (d, J = 8.8 Hz, 2H), 3.82 (s, 3H), 2.91 (t, J =
.1 Hz, 2H), 1.64–1.45 (m, 4H), 0.97 (t, J = 7.4 Hz, 3H).
4
1:22<4176::AID-ANIE4176>3.0.CO;2-U.
(
2) (a) Littke, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc.
2002, 124 (22), 6343. and references cited therein. doi:10.
1021/ja020012f; (b) Kim, Y. M.; Yu, S. J. Am. Chem. Soc.
Trimethyl(2-phenyl-1-ethynyl)silane (Table 2, entry 11)
2
6 1
Oil. H NMR (CDCl , 300 MHz) d: 7.47–7.43 (m, 2H),
3
2
003, 125 (7), 1696. doi:10.1021/ja028966t; (c) Menzel, K.;
7
.31–7.28 (m, 3H), 0.24 (m, 9H).
Fu, G. C. J. Am. Chem. Soc. 2003, 125 (13), 3718. doi:10.
1021/ja0344563; (d) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J.
Am. Chem. Soc. 2003, 125 (47), 14288. doi:10.1021/
ja037043a; (e) Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc.
Trimethyl[(4-nitrophenyl)ethynyl]silane (Table 2, entry 12)
1
0 1
Oil. H NMR (CDCl , 300 MHz) d: 8.16 (d, J = 8.7 Hz,
3
2
H), 7.61 (d, J = 8.7 Hz, 2H), 0.18 (s, 9H).
2
003, 125 (50), 15292. doi:10.1021/ja038328q; (f) Wolf, C.;
Lerebours, R. J. Org. Chem. 2003, 68 (18), 7077. doi:10.1021/
jo034758n; (g) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68
(
E)-1-(3-Methoxyprop-1-enyl)benzene (Table 3, entry 1)
16 1
Oil. H NMR (CDCl , 300 MHz) d: 7.42–7.20 (m, 5H),
3
(
19), 7551. doi:10.1021/jo0347056; (h) Mazzola, R. D., Jr;
6
6
.62 (d, J = 15.9 Hz, 1H), 6.27–6.30 (m, 1H), 4.04 (d, J =
Giese, S.; Benson, C.; West, F. G. J. Org. Chem. 2004, 69 (1),
.1 Hz, 2H), 3.37 (s, 3H).
2
20. doi:10.1021/jo034788q; (i) Högenauer, K. Synlett 2001,
2
001 (6), 878. doi:10.1055/s-2001-14619; (j) Scrivanti, A.;
(
E)-1-Methoxy-4-styrylbenzene (Table 3, entry 2)
Matteoli, U.; Beghetto, V.; Antonaroli, S.; Crociani, B.
Tetrahedron 2002, 58 (34), 6881. doi:10.1016/S0040-4020
1
6
1
mp 135–136 °C (lit. mp 134–135 °C). H NMR (CDCl ,
00 MHz) d: 7.52 (d, J = 7.5 Hz, 2H), 7.47 (d, J = 8.6 Hz,
H), 7.35 (t, J = 7.5 Hz, 2H), 7.27–7.22 (m, 1H), 7.09 (d,
3
4
(
02)00733-0; (k) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J.
Tetrahedron Lett. 2004, 45 (38), 7057. doi:10.1016/j.tetlet.
004.07.126.
2
J = 16.7 Hz, 1H), 7.00 (d, J = 16.7 Hz, 1H), 6.92 (d, J =
2
8
.7 Hz, 2H), 3.85 (s, 3H).
(
3) (a) Herrmann, W. A.; Öfele, K.; von Preysing, D.; Schneider,
S. K. J. Organomet. Chem. 2003, 687 (2), 229. doi:10.1016/j.
jorganchem.2003.07.028; (b) Hillier, A. C.; Grasa, G. A.;
Viciu, M. S.; Lee, H. M.; Yang, C.; Nolan, S. P. J. Organomet.
Chem. 2002, 653 (1–2), 69. doi:10.1016/S0022-328X(02)
(
Z)-1-Methyl-4-styrylbenzene (Table 3, entry 3)
1
6 1
Oil. H NMR (CDCl , 400 MHz) d: 7.30–7.20 (m, 5H),
3
7
2
.17 (d, J = 8.0 Hz, 2H), 7.06 (d, J = 8.0 Hz, 2H), 6.60 (s,
H), 2.34 (s, 3H).
0
1154-3.
4) (a) Alonso, D. A.; Nájera, C.; Pacheco, M. C. Org. Lett. 2000,
(13), 1823. doi:10.1021/ol0058644; (b) Choudary, B. M.;
(
(
E)-1-(Hex-1-enyl)-4-methoxybenzene (Table 3, entry 4)
2
16 1
Oil. H NMR (CDCl , 400 MHz) d: 7.25 (d, J = 8.5 Hz,
3
Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J.
Am. Chem. Soc. 2002, 124 (47), 14127. doi:10.1021/
ja026975w; (c) Amatore, C.; Bahsoun, A. A.; Jutand, A.;
Meyer, G.; Ntepe, A. N.; Ricard, L. J. Am. Chem. Soc. 2003,
2
5
2
H), 6.82 (d, J = 8.5 Hz, 2H), 6.29 (d, J = 15.4 Hz, 1H),
.93 (dt, J = 15.4, 7.0 Hz, 1H), 3.82 (s, 3H), 2.20–2.15 (m,
H), 1.45–1.33 (m, 4H), 0.91 (t, J = 7.0 Hz, 3H).
1
25 (14), 4212. doi:10.1021/ja0204978; (d) Minière, S.;
(
Z)-1-Nitro-4-styrylbenzene (Table 3, entry 5)
Cintrat, J.-C. J. Org. Chem. 2001, 66 (22), 7385. doi:10.
1021/jo015824t.
1
6
1
mp 60–62 °C (lit. mp 60.5–61.5 °C). H NMR (CDCl ,
3
4
2
00 MHz) d: 8.10 (d, J = 8.7 Hz, 2H), 7.40 (d, J = 8.7 Hz,
H), 7.25–7.18 (m, 5H), 6.80 (d, J = 12.5 Hz, 1H), 6.60 (d,
(5) van Asselt, R.; Elsevier, C. J. Tetrahedron 1994, 50 (2), 323.
doi:10.1016/S0040-4020(01)80757-2.
(6) (a) Clapham, B.; Reger, T. S.; Janda, K. D. Tetrahedron 2001,
J = 12.5 Hz, 1H).
5
7 (22), 4637. doi:10.1016/S0040-4020(01)00298-8; (b)
(
Z)-1-(Hex-1-enyl)-4-nitrobenzene (Table 3, entry 6)
Schwarz, J.; Bohm, V. P. W.; Gardiner, M. G.; Grosche, M.;
Herrmann, W. A.; Hieringer, W.; Raudaschl-Sieber, G.
Chemistry 2000, 6 (10), 1773. doi:10.1002/(SICI)1521-3765
(20000515)6:10<1773::AID-CHEM1773>3.0.CO;2-P.
16 1
Oil. H NMR (CDCl , 400 MHz) d: 8.20 (d, J = 8.6 Hz,
3
2
5
1
H), 7.40 (d, J = 8.6 Hz, 2H), 6.44 (d, J = 11.5 Hz, 1H),
.84 (dt, J = 11.5, 7.0 Hz, 1H), 2.35–2.30 (m, 2H), 1.49–
.43 (m, 2H), 1.39–1.33 (m, 2H), 0.89 (t, J = 7.0 Hz, 3H).
(7) (a) Nasrollahzadeh, M.; Bayat, Y.; Habibi, D.; Moshaee, S.
Tetrahedron Lett. 2009, 50 (31), 4435. doi:10.1016/j.tetlet.
2009.05.048; (b) Habibi, D.; Nasrollahzadeh, M. Synth.
Acknowledgement
Commun.
0
2010,
40
(21),
3159.
doi:10.1080/
We are thankful to the Islamic Azad University, Ahar
Branch, for partial support of this research.
0397910903370683; (c) Modarresi-Alam, A. R.; Nasrollah-
zadeh, M.; Khamooshi, F. Arkivoc 2007, (xvi), 234; (d)
Modarresi-Alam, A. R.; Khamooshi, F.; Nasrollahzadeh, M.;
Amirazizi, H. A. Tetrahedron 2007, 63 (36), 8723. doi:10.
1016/j.tet.2007.06.048; (e) Mohammadi, B.; Hosseini Jamkar-
ani, S. M.; Kamali, T. A.; Nasrollahzadeh, M.; Mohajeri, A.
Turk. J. Chem 2010, 34, 613 doi:10.3906/kim-0906-28; (f)
Nasrollahzadeh, M.; Habibi, D.; Shahkarami, Z.; Bayat, Y.
Tetrahedron 2009, 65 (51), 10715. doi:10.1016/j.tet.2009.10.
029; (g) Habibi, D.; Nasrollahzadeh, M.; Bayat, Y. Synth.
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