Aires da Concei c¸ a˜ o Silva et al. / Journal of Organometallic Chemistry 692 (2007) 3104–3107
3107
1
-Biphenyl-4-yl-ethanone. White solid, 0.180 g (92%).
(c) J.K. Stille, Angew. Chem., Int. Ed. 25 (1986) 508;
(d) M. Kosugi, K. Sasazawa, Y. Shimizu, T. Migita, Chem. Lett.
1977) 1423.
5] (a) E. Negishi, A.O. King, N. Okukado, J. Organomet. Chem. 42
(1977) 1821;
1
M.p.: 121–122 °C. H NMR (CDCl , 200 MHz) d 8.09
d, 2H), 7.63 (d, 2H), 7.58 (d, 2H), 7.40 (dd, H), 7.37
dd, H), 2.63 (s, 1H). C NMR (CDCl , 50 MHz) d
3
(
(
(
[
1
3
3
1
97.7, 145.7, 139.8, 135.9, 128.9, 128.1, 127.3, 26.2. GC–
(b) A.O. King, N. Okukado, E. Negishi, J. Chem. Soc., Chem.
Commun. (1977) 683.
[6] (a) K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 16
(1975) 446;
MS: 196 m/z, 181 m/z, 153 m/z, 77 m/z, 43 m/z.
0
1
-(4 -Fluoro-biphenyl-4-yl)-ethanone.
White
solid,
1
0
2
2
5
1
.205 g (96%). M.p.: 109–110 °C. H NMR (CDCl3,
(
b) K.J. Sonogashira, J. Organomet. Chem. 653 (2002) 46.
00 MHz) d 8.00 (d, 2H), 7.63 (d, 2H), 7.59–7.57 (m,
[
7] (a) Y. Dawei, T. Yao, R.C. Larock, J. Org. Chem. 71 (2006) 62;
(b) G.A. Molander, D.E. Petrillo, N.R. Landzberg, J.C. Rohanna,
B. Biolatto, Synlett (2005) 1763;
1
3
H), 7.17 (t, 2H), 2.64 (s, 3H). C NMR (CDCl3,
0 MHz) d 197.7, 164.2, 161.7, 144.7, 135.9, 135.8, 129.0,
28.9, 127.0, 116.1, 115.9, 26.7. GC–MS: 214 m/z, 199 m/
(
c) B. Blanco, M. Brissart, M. Moreno-Manas, R. Pleixats, A.
Mehdi, C. Reye, S. Bouquillon, F. Henin, J. Muzart, J. Appl. Catal.
A. General 297 (2006) 117;
z, 171 m/z, 94 m/z, 77 m/z.
-Fluoro-biphenyl. White solid, 0.162 g (94%). M.p.:
4
(
d) J. Masllorens, S. Bouquillon, A. Roglans, F. Henin, J. Muzart, J.
Organomet. Chem. 690 (2005) 3822.
[8] (a) D. Astruc, F. Lu, J.R. Aranzaes, Angew. Chem., Int. Ed. 44
1
7
7
5
1
5 °C. H NMR (CDCl , 200 MHz) d 7.56–7.53 (m, 4H),
3
13
.40 (t, 2H), 7.33 (t, 1H), 7.15 (t, 2H). C NMR (CDCl3,
0 MHz) d 163.7, 161.3, 140.3, 137.4, 137.3, 128.8, 128.7,
28.6, 127.3, 127.0, 115.7, 115.5. GC–MS: 172 m/z, 153
(
(
2005) 7852;
b) C. Li, Chem. Rev. 105 (2005) 3095.
[
9] (a) Y. Li, X.M. Hong, D.M. Collard, M.A. El-Sayed, Org. Lett. 2
15) (2000) 2385;
(b) R. Narayanan, M.A. El-Sayed, J. Catal. 234 (2005) 348.
m/z, 95 m/z, 77 m/z.
-Phenylfuran. Colorless liquid, 0.111 g (77%). H NMR
CDCl , 200 MHz) d 7.68 (t, 2H), 7.44 (d, 1H), 7.39–7.24
(
1
2
(
(
[10] (a) J. Li, X. Hu, Y. Liang, Y. Xie, Tetrahedron 62 (2006) 31;
(b) L. Liu, Y. Zhang, Y. Wang, J. Org. Chem. 70 (2005) 6122;
3
1
3
m, 3H), 6.64 (d, 1H), 6.45 (dd, 1H). C NMR (CDCl3,
(
(
(
c) N. Jiang, A.J. Ragarskas, Tetrahedron Lett. 47 (2006) 197;
d) M. Lysen, K. Koehler, Synlett (2005) 1671;
e) G. Zhang, J. Chem. Res. (2004) 593;
5
1
0 MHz) d 154.2, 142.3, 131.1, 128.9, 127.5, 124.0, 111.8,
05.1. GC–MS: 144 m/z, 115 m/z, 77 m/z, 65 m/z.
1
2
-Phenylthiophene. Colorless liquid, 0.126 g (79%). H
(f) G. Cravotto, M. Beggiato, A. Penoni, G. Palmisano, S. Tollari,
v eˆ que, W. Bonrath, Tetrahedron Lett. 46 (2005) 2267;
J.M. Le
(g) M. Nishida, T. Tagata, J. Synth. Org. Chem. Jpn. 62 (2004)
37;
h) T. Tagata, M. Nishida, J. Org. Chem. 68 (2003) 9412.
11] (a) J.D. Revell, A. Ganesan, Org. Lett. 4 (18) (2002) 3071;
b) C.W. Scheeren, G. Machado, J. Dupont, P.F.P. Fichtner, S.R.
Texeira, Inorg. Chem. 42 (2003) 4738;
´
NMR (CDCl , 200 MHz) d 7.61 (d, 1H), 7.37–7.16 (m,
3
1
3
5
H), 7.02–6.99 (m, 2H). C NMR (CDCl , 50 MHz) d
3
7
(
1
28.9, 127.9, 127.9, 127.4, 125.9, 124.8, 123.0, 29.7. GC–
MS: 160 m/z, 82 m/z, 77 m/z.
[
(
Acknowledgements
(
(
c) M.B. Andrus, C. Song, Org. Lett. 3 (23) (2001) 3761;
d) C.J. Mathews, P.J. Smith, T. Welton, J. Mol. Catal. A: Chem.
Financial support from CNPq, CAPES and FAPERJ,
Brazilian Governmental Financing Agencies is gratefully
acknowledged.
2
14 (2004) 27;
(
e) C.J. Mathews, P.J. Smith, T. Welton, Chem. Commun. (2000)
1249.
[
[
12] A.S. Castanet, F. Colobert, J.R. Desmurs, T. Schlama, J. Mol. Catal.
A: Chem. 182 (2002) 481.
13] (a) T.N. Glasnov, W. Stadlbauer, C.O. Kappe, J. Org. Chem. 70
References
(
2005) 3864;
[
1] (a) K.C. Nicolaou, P.G. Bulger, D. Sarlah, Angew. Chem., Int. Ed.
4 (2005) 4442;
(b) G. Miao, P. Ye, Y. Libing, C.M. Baldino, J. Org. Chem. 70
(2005) 2332;
4
(
(
(
b) J. Muzart, Tetrahedron 61 (2005) 4179;
c) E. Negishi, J. Organomet. Chem. 653 (2002) 34;
d) J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M. Lamaire, Chem.
(c) Y. Gong, W. He, Org. Lett. 4 (22) (2002) 3803.
[14] (a) G. Cravotto, M. Beggiato, A. Penoni, G. Palmisano, S. Tollari,
J. L e´ v eˆ quec, W. Bonrath, Tetrahedron Lett. 46 (2005) 2267;
(b) G. Cravotto, G. Palmisano, S. Tollari, G.M. Nano, A. Penoni,
Ultrason. Sonochem. 12 (2005) 91;
Rev. 102 (2002) 1359.
2] (a) A. Suzuki, Acc. Chem. Res. 15 (1982) 178;
[
(
b) N. Miyaura, T. Yanagi, A. Suzuki, Synth. Commun. 11 (1981) 513.
(c) R. Rajagopal, D.V. Jarikote, K.V. Srinivasan, Chem. Commun.
(2002) 616;
(d) V. Polackova, M. Hutka, S. Toma, Ultrason. Sonochem. 12
(2005) 99.
[
[
3] R.F. Heck, J.P. Nolley Jr., J. Org. Chem. 37 (1972) 2320.
4] (a) D. Milstein, J.K. Stille, J. Am. Chem. Soc. 100 (1978) 3636;
(b) D. Milstein, J.K. Stille, J. Am. Chem. Soc. 101 (1979) 4992;