3
592
N. Nishiwaki et al. / Tetrahedron Letters 51 (2010) 3590–3592
PdOAc
+
PdOAc
Ph
Pd(OAc) (1 mol%)
2
Ph
+
+
Ph
HFIP, rt, 1 h
H
H
6
8
7
(82%)
10a
6
11a
11b
PdCl
Ph
PdCl (MeCN) (1 mol%)
PdCl
2
2
CH Cl /HFIP (1/1)
+
2
2
Ph
Ph
4
0 °C, 0.5 h
10b
9
(71%)
8
Scheme 2. Dimerization of styrene 6 and a-methylstyrene 8 using a catalyst system of Pd(II)–HFIP.
1
2. Ravikumar, K. S.; Zhang, Y. M.; Bégué, J.-P.; Bonnet-Delpon, D. Eur. J. Org. Chem.
998, 2937–2940.
3. Jinesh, C. M.; Antonyraj, C. A.; Kannan, S. Catal. Today 2009, 141, 176–
81.
1
1
[
Pd] : palladium species
Me
+
[Pd]
1
1
d
14. Qafisheh, N.; Mukhopadhyay, S.; Joshi, A. V.; Sasson, Y.; Chuah, G.-K.; Jaenicke,
S. Ind. Eng. Chem. Res. 2007, 46, 3016–3023.
15. Yu, Z.; Yan, S.; Zhang, G.; He, W.; Wang, L.; Li, Y.; Zeng, F. Adv. Synth. Catal.
2
006, 348, 111–117.
PdOAc
PdOAc
+
16. Potapov, D. A.; Tjurina, L. A.; Smirnov, V. V. Russ. Chem. Bull., Int. Ed. 2005, 54,
Me
Me
1185–1188.
1
7. Wu, W.; Verkade, J. G. ARKIVOC 2004, ix, 88–95.
5
b
18. Aramendia, M. A.; Borau, V.; Jiménez, C.; Marinas, A.; Marinas, J. M.; Urbano, F.
J. J. Catal. 2002, 211, 556–559.
Figure 1. Substituent effect of a methyl group.
19. Donohoe, T. J.; O’Riordan, T. J. C.; Rosa, C. P. Angew. Chem., Int. Ed. 2009, 48,
1014–1017.
20. Sparke, M. B.; Turner, L.; Wenham, A. J. M. J. Catal. 1965, 4, 332–340.
2
1. Beach, N. J.; Blacquiere, J. M.; Drouin, S. D.; Fogg, D. E. Organometallics 2009, 28,
+
441–447.
PdOAc
PdOAc
22. Hanessian, S.; Giroux, S.; Larsson, A. Org. Lett. 2006, 8, 5481–5484.
δ+
MeO
+
δ+
MeO
2
2
3. Wipf, P.; Spencer, S. R. J. Am. Chem. Soc. 2005, 127, 225–235.
4. Schmidt, B. Eur. J. Org. Chem. 2004, 1865–1880.
[
Pd] 5e
[
Pd]
25. Cadierno, V.; García-Garrido, S. E.; Gimeno, J. Chem. Commun. 2004, 232–
33.
2
2
2
2
6. Urbala, M.; Kúznik, N.; Krompiec, S.; Rzepa, J. Synlett 2004, 1203–1206.
7. Morrill, T. C.; D’Souza, C. A. Organometallics 2003, 22, 1626–1629.
8. Kameda, N.; Yoneda, T. Nippon Kagaku Kaishi 2000, 677–683.
δ+
O
Me
[Pd]
[Pd]
29. Shen, X.; Wasmuth, A. S.; Zhao, J.; Zhu, C.; Nelson, S. G. J. Am. Chem. Soc. 2006,
28, 7438–7439.
30. Baxendale, I. R.; Lee, A.-L.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 2002, 1850–
857.
1. All of allylbenzenes
References are shown in Supplementary data.
32. In catalytic reaction using Pd(OAc)
involvement of such
depicted; see Refs. 41 and 42.
3. The carbonium cation 4 could be formed via coordination of Pd(OAc)
O
Me
1
1
1
g
3
1 and propenylbenzenes 2 are known compounds.
Figure 2. Substituent effect of a methoxy group.
a
2
,
a
species is
3
2
to the
double bond of 1 and subsequent elimination of acetate ion. There is no reason
Supplementary data
to disregard this process; however, in order to emphasize the importance of
+
cationic species in the present reaction, the pathway involving PdOAc cation 3
is depicted in the light of references.4
1,42
3
4. The present isomerization is also accounted for by the pathway involving (
p-
allyl)PdOAc formed via coordination of Pd(OAc) to the double bond of 1.
2
However, the substituent effects observed is not likely supported by this
mechanism, because it does not lead to cationic species explicitly.
5. Taylor, J. G.; Whittall, N.; Hii, K. K. Org. Lett. 2006, 8, 3561–3564.
References and notes
3
1
2
3
4
5
6
7
8
9
.
.
.
.
.
.
.
.
.
A review: Shuklov, I. A.; Dubrovina, N. V.; Börner, A. Synthesis 2007, 2925–2943.
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Tanabe, H.; Ichikawa, J. Chem. Lett. 2010, 39, 248–249.
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37. Sun, H.-B.; Li, B.; Hua, R.; Yin, Y. Eur. J. Org. Chem. 2006, 4231–4236.
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643. Chem. Abstr. 2000, 133, 135121.
39. Under similar conditions,
a-phenylstylene also affords the corresponding
indane (89% yield), suggesting that the stabilization of benzyl cation by
phenyl or methyl group results in the cyclization as shown in Scheme 2.
a-
Sato, H.; Tojima, H.; Ikimi, K. J. Mol. Cat. A: Chem. 1999, 144, 285–293.
Shigehisa, H.; Takayama, J.; Honda, T. Tetrahedron Lett. 2006, 47, 7301–7306.
40. Doherty, S.; Knight, J. G.; Smyth, C. H.; Harrington, R. W.; Clegg, W.
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1
0. Ben-Daniel, R.; de Visser, S. P.; Shaik, S.; Neumann, R. J. Am. Chem. Soc. 2003,
25, 12116–12117.
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002, 41, 4481–4484.
1
1
2
42. Sen, A.; Lai, T.-W. Organometallics 1983, 2, 1059–1060.