V. Polaꢀcꢁkovaꢀ et al. / Tetrahedron 63 (2007) 8742–8745
8745
J¼7.2 Hz, 1H); 6.20 (dd, J¼15.6, 1.5 Hz, 1H), 6.66 (dd,
Acknowledgements
J¼15.6 Hz, 7.2 Hz, 1H), 7.16–7.38 (m, 14H). 13C NMR
(CDCl3, 75 Hz): d 143.0, 141.7, 137.5, 136.6, 132.7,
131.5, 130.7, 129.1, 128.7, 128.6, 128.5, 127.4, 126.7,
126.5, 126.4, 126.2, 50.5, 20.0. GC–MS: 284 (78, M+),
269 (100), 206 (25), 191 (61), 178 (50), 165 (29), 115
(43), 91 (32). Anal. Calcd for C22H20 (284.38): C, 92.91;
H, 7.09. Found: C, 93.03; H, 7.01.
The authors thank Dr. B. Horvath and his staff for 1H NMR
and 13C NMR analyses and Dr. R. Kubinec and his staff for
GC–MS analyses, both from the Institute of Chemistry of
Faculty of Natural Sciences, Comenius University. Our
thanks are due also to M. Hut’ka for preliminary experi-
ments on the Biotage Initiator reactor. This work was carried
out under the auspicies of the COST D32/0010/04 project
and financial help from the Ministry of Education of the Slo-
vak Republic (VTP project no.1012/2003) is acknowledged.
4.2.3. rac-(E)-1,3-Diphenyl-3-[(4-trifluoromethyl)phen-
yl]prop-1-ene [3f]. Colorless oil. 1H NMR (CDCl3,
300 Hz): d 4.94 (d, J¼7.5 Hz, 1H), 6.35 (d, J¼15.9 Hz,
1H), 6.64 (dd, J¼15.9, 7.5 Hz, 1H), 7.21–7.49 (m, 12H),
7.57 (d, J¼8 Hz, 2H). 13C NMR (CDCl3, 75 Hz): d 147.8
(q, J¼1.2 Hz), 142.0, 137.1, 132.4, 131.7, 129.2, 128.9,
128.8 (q, J¼8.1 Hz), 128.8, 127.9, 127.0, 126.6, 125.6 (q,
J¼3.8 Hz), 124.5 (q, J¼272 Hz), 54.2. GC–MS: 338 (90,
M+), 260 (100), 191 (50), 178 (45), 165 (33), 91 (27).
References and notes
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4.2.4. rac-(E)-1,3-Diphenyl-3-[(3-trifluoromethyl)phen-
yl]prop-1-ene [3g]. White crystals, mp 48–49 ꢀC (from n-
1
hexane). H NMR (CDCl3, 300 Hz): d 4.95 (d, J¼7.5 Hz,
1H), 6.36 (d, J¼15.6 Hz, 1H), 6.64 (dd, J¼15.6, 7.5 Hz,
1H), 7.21–7.50 (m, 14H). 13C NMR (CDCl3, 75 Hz):
d 144.5, 142.6, 136.9, 132.2, 132.1 (q, J¼1.3 Hz), 131.5,
130.8 (q, J¼32 Hz), 128.9, 128.7, 128.6, 127.6, 126.8,
126.4, 125.3 (q, J¼3.6 Hz), 123.4 (q, J¼3.7 Hz), 124.2 (q,
J¼271 Hz), 54.0. GC–MS: 338 (88, M+), 260 (100), 191
(35), 178 (33), 115 (25), 91 (19).
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6. Polackova, V.; Toma, S.; Augustınova, I. Tetrahedron 2006, 62,
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4.2.5. rac-(E)-1,3-Diphenyl-3-[(2-trifluoromethyl)phen-
yl]prop-1-ene [3h]. White crystals, mp 49–51 ꢀC (from n-
1
hexane). H NMR (CDCl3, 300 Hz): d 5.37 (d, J¼7.5 Hz,
1H), 6.29 (d, J¼15.9 Hz, 1H), 6.62 (dd, J¼15.9, 7.5 Hz,
1H), 7.22–7.38 (m, 12H), 7.50 (t, J¼15 Hz, 1H); 7.69 (d,
J¼7.8 Hz, 1H). 13C NMR (CDCl3, 75 Hz): d 143.1, 142.3
(q, J¼1.5 Hz), 137.0, 132.2, 131.9 (q, J¼1.1 Hz), 131.7,
131.1, 128.6, 128.4, 127.5, 126.5, 126.4, 126.3, 125.9 (q,
J¼6.7 Hz), 124.5 (q, J¼272 Hz), 48.7. GC–MS: 338 (100,
M+), 269 (22), 260 (80), 191 (33), 179 (30), 115 (26), 91 (22).
13. Bouyssi, D.; Gerusz, V.; Balme, G. Eur. J. Org. Chem. 2002,
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14. Legros,J.-Y.;Fiaud,J.-C.Tetrahedron Lett. 1990,31, 7453–7456.
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2004, 346, 1798–1822.
16. Books: (a) Microwaves in Organic Synthesis, 2nd ed.; Loupy,
A., Ed.; Wiley-VCH: Weinheim, 2006; (b) Kappe, C. O.;
Stadler, A. Microwaves in Organic and Medicinal Chemistry;
Wiley-VCH: Weinheim, 2005; (c) Microwave-Assisted
4.2.6. rac-(E)-1,3-Diphenyl-3-(4-chlorophenyl)prop-1-
ene [3i]. White crystals, mp 62–63.5 ꢀC (from n-hexane).
1H NMR (CDCl3, 300 Hz): d 4.86 (d, J¼7.2 Hz, 1H), 6.33
(d, J¼15.9 Hz, 1H), 6.62 (dd, J¼15.9, 7.2 Hz, 1H); 7.15–
7.38 (m, 14H). 13C NMR (CDCl3, 75 Hz): d 142.9, 141.9,
136.9, 132.2, 131.9, 131.7, 129.9, 128.5, 127.4, 126.6,
126.2. GC–MS: 304 (71, M+), 269 (75), 226 (45), 191
(100), 178 (46), 165 (46), 115 (25), 91 (25). Anal. Calcd
for C21H17Cl (304.81): C, 82.74; H, 5.62; Cl, 11.63. Found:
C, 82.94; H, 5.89; Cl, 10.93.
€
Organic Synthesis; Lidstrom, P., Tierney, J. P., Eds.;
Blackwell Publishing: Oxford, 2005; (d) Hayes, B. L.
Microwave Synthesis: Chemistry at the Speed of Light; CEM
Publishing: Matthews, NC, 2002.
17. Recent reviews: (a) Kappe, C. O. Angew. Chem., Int. Ed. 2004,
43, 6250–6284; (b) Hayes, B. L. Aldrichim. Acta 2004, 37, 66–
77; (c) De La Hoz, A.; Diaz-Ortiz, A.; Moreno, A. Chem. Soc.
Rev. 2005, 34, 164–178.
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8924.
19. Kobayashi, Y.; Tokoro, Y.; Watatani, K. Eur. J. Org. Chem.
2000, 3825–3834.
20. Kabalka, G. W.; Dong, G.; Venkataiah, B. Org. Lett. 2003, 5,
893–895.
4.2.7. rac-(E)-1,3-Diphenyl-3-(1-naphthyl)prop-1-ene
[3j]. Colorless oil. 1H NMR (CDCl3, 300 Hz): d 5.66 (d, J¼
7.2 Hz, 1H), 6.26 (dd, J¼15.9, 1.2 Hz, 1H), 6.81 (dd, J¼
15.9, 7.2 Hz, 1H), 7.20–7.45 (m, 14H), 7.78 (d, J¼7.8 Hz,
1H), 7.85–7.88 (m, 1H), 8.03–8.06 (m, 1H). 13C NMR
(CDCl3, 75 Hz): d 143.3, 139.3, 137.5, 134.2, 132.8,
132.0, 131.9, 129.1, 128.9, 128.7, 127.6, 127.5, 126.7,
126.5, 126.2, 125.7, 125.6, 124.3, 50.3. GC–MS: 320 (100,
M+), 241 (42), 229 (99), 215 (36), 165 (30), 115 (25), 91
(22). Anal. Calcd for C25H20 (320.43): C, 93.71; H, 6.29.
Found: C, 94.05; H, 6.39.
21. Ramarao, Ch.; Ley, S. V.; Smith, S. C.; Shirley, I. M.;
DeAlmeida, N. Chem. Commun. 2002, 1132–1133.