ALKYNYLATION OF ARYL IODIDES
183
1
3
7
.56–7.50 (m, 3H), 7.42–7.38 (m, 3H). C NMR (100 MHz, CDCl ): d 148.3, 137.1,
3
1
32.1, 129.6, 129.4, 128.2, 126.6, 124.9, 122.9, 122.3, 92.1, 87.0.
[16]
ꢀ ꢀ
1
-(4-Acetylphenyl)phenylacetylene (3f). Mp 94–95 C (lit. 95–96 C). IR
ꢁ
1
1
(
KBr): t (cm ) 3080, 2918, 2223, 1685, 1606, 1265, 835, 697. H NMR (400 MHz,
CDCl ): d 7.98 (d, J ¼ 8.0 Hz, 2H), 7.63 (d, J ¼ 8.0 Hz, 2H), 7.52 (d, J ¼ 2.4 Hz,
3
1
3
2
H), 7.40–7.37 (m, 3H), 2.60 (s, 3H). C NMR (100 MHz, CDCl ): d 197.7,
3
1
36.4, 131.9, 131.6, 128.7, 128.5, 128.2, 128.1, 122.6, 92.9, 88.8, 26.5.
ꢀ
[17]
ꢀ
73–74 C).
1
-(4-Methylphenyl)phenylacetylene (3g). Mp 73–74 C (lit.
ꢁ
1
1
IR (KBr): t (cm ) 3030, 2918, 2860, 2215, 1596, 1510, 818, 697. H NMR
(
3
1
400 MHz, CDCl ): d 7.55–7.52 (m, 2H), 7.42 (d, J ¼ 8.0 Hz, 2H), 7.36–7.29 (m,
3
1
3
H), 7.16 (d, J ¼ 8.0 Hz, 2H), 2.38 (s, 3H). C NMR (100 MHz, CDCl ): d 138.5,
3
31.6, 131.4, 129.2, 128.4, 128.1, 123.8, 120.1, 89.6, 88.7, 21.7.
[17]
ꢀ ꢀ
1
-(4-Methoxyphenyl)phenylacetylene (3h). Mp 59–60 C (lit. 58–59 C).
1
ꢁ
1
IR (KBr): t (cm ) 3025, 2212, 1604, 1500, 1240, 835, 750, 695. H NMR (400 MHz,
1
3
CDCl ): d 7.52–7.43 (m, 4H), 7.31–7.28 (m, 3H), 6.86–6.83 (m, 2H), 3.75 (s, 3H).
C
3
NMR (100 MHz, CDCl ): d 159.6, 133.0, 131.6, 128.3, 128.0, 123.4, 115.6, 113.9,
3
8
9.6, 88.1, 55.4.
[
18]
1
-Phenyl-2-(trimethylsilyl)acetylene (3i). Colorless liquid.
IR (neat): t
ꢁ
1
cm ) 3080, 2160, 1598, 1490, 1250, 860, 755, 690. H NMR (400 MHz, CDCl ):
d 7.47–7.44 (m, 2H), 7.31–7.29 (m, 3H), 0.27 (s, 9H). C NMR (100 MHz, CDCl3):
d 132.1, 128.4, 128.2, 123.0, 105.1, 94.2, 0.01.
1
(
3
1
3
[
18]
1
-(4-Methoxyphenyl)-2-(trimethylsilyl)acetylene (3j). Colorless liquid.
ꢁ
1
1
IR (neat): t (cm ) 2155, 1605, 1510, 1250, 835, 755, 700. H NMR (400 MHz, CDCl ):
3
1
3
d 7.43 (d, J ¼ 8.8 Hz, 2H), 6.80 (d, J ¼ 8.8 Hz, 2H), 3.80 (s, 3H), 0.25 (s, 9H). C NMR
(
100 MHz, CDCl ): d 159.6, 133.7, 115.1, 113.9, 105.4, 92.5, 55.2, 0.07.
3
ACKNOWLEDGMENTS
The authors thank the Research Council of Shahrood University of
Technology for the support of this work.
REFERENCES
1
. Sonogashira, K.; Tohda, Y.; Hagihara, N. A convenient synthesis of acetylenes: Catalytic
substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes, and bromopyridines.
Tetrahedron Lett. 1975, 16, 4467–4470.
2
3
4
5
. Moore, J. S. Shape-persistent molecular architectures of nanoscale dimension. Acc. Chem.
Res. 1997, 30, 402–413.
2
. Tykwinski, R. R. Evolution in the palladium-catalyzed cross-coupling of sp- and sp -
hybridized carbon atoms. Angew. Chem. Int. Ed. 2003, 42, 1566–1568.
. Negishi, E.-J.; Anastasia, L. Palladium-catalyzed alkynylation. Chem. Rev. 2003, 103,
1979–2018.
. Chow, H.-F.; Wan, C.-W.; Low, K.-H.; Yeung, Y.-Y. A highly selective synthesis of
diarylethynes and their oligomers by a palladium-catalyzed Sonogashira coupling reaction
under phase transfer conditions. J. Org. Chem. 2001, 66, 1910–1913.