Palladium Nanoparticle-Cored Dendrimers
concentrated to give the products. The products were purified by
column chromatography over silica gel using hexane as eluent.
[14] M. Brust, M. Walker, D. Bethel, D. J. Schiffrin, J. Chem. Soc.,
Chem. Commun. 1994, 801–802.
[
[
[
[
15] L. Wu, B.-L. Li, Y.-Y. Huang, H.-F. Zhou, Y.-M. He, Q.-H.
1 4
Comparison of the Activities of Pd-G –Pd-G
Fan, Org. Lett. 2006, 8, 3605–3608.
16] L. Wu, Z.-W. Li, F. Zhang, Y.-M. He, Q.-H. Fan, Adv. Synth.
Catal. 2008, 350, 846–862.
Suzuki Coupling: The reaction was carried out with 4-cyanophen-
ylboronic acid (0.4 mmol) and 4-iodoanisole (0.4 mmol) in THF
17] V. K. R. Kumar, K. R. Gopidas, Chem. Asian J. 2010, 5, 887–
3 4
(5.0 mL) in the presence of aqueous K PO (1 mmol) under reflux
896.
conditions for 6 h. The catalyst loading was 1 mg for each genera-
tion. After the reaction time, the reaction mixture was worked up
and the products were isolated by column chromatography over
silica gel.
18] J. Pinson, F. Podvorica, Chem. Soc. Rev. 2005, 34, 429–439.
[19] D. Bélanger, J. Pinson, Chem. Soc. Rev. 2011, 40, 3995–4048.
[20] S. Mahouche-Chergui, S. Gam-Derouich, C. Mangeney, M. M.
Chehimi, Chem. Soc. Rev. 2011, 40, 4143–4166.
[
21] F. Mirkhalaf, J. Paprotny, D. J. Schiffrin, J. Am. Chem. Soc.
006, 128, 7400–7401.
Hiyama Coupling: Trimethoxy(phenyl)silane (2 mmol), 4-iodo-
anisole (1 mmol) and a solution of tetrabutylammonium fluoride
2
[
22] V. K. R. Kumar, K. R. Gopidas, Tetrahedron Lett. 2011, 52,
(1.0 m, 2.0 mL) were added to dry THF (5.0 mL) and heated at
3102–3105.
reflux for 24 h. The catalyst loading was 1.0 mg for each genera- [23] J. M. J. Fréchet, H. Ihre, M. Davey, in: Dendrimers and Other
tion. After the reaction time, the reaction mixture was extracted
with distilled water and the organic layer was concentrated to ob-
tain the product, which was further purified by column chromatog-
raphy over silica gel using hexane as eluent.
Dendritic Polymers (Eds.: D. A. Tomalia, J. M. J. Fréchet),
Wiley, Chichester, UK, 2001, chapter 24, p. 569.
[
24] S. M. Grayson, J. M. J. Fréchet, Chem. Rev. 2001, 101, 3819–
3867, and references cited therein.
[
25] D. Ghosh, S. Chen, J. Mater. Chem. 2008, 18, 755–762.
Supporting Information (see footnote on the first page of this arti-
[26] R. H. Terrill, T. A. Postlethwaite, C.-H. Chen, C.-D. Poon, A.
Terzis, A. Chen, J. E. Hutchison, M. R. Clark, G. Wignall, J. D.
Londono, R. Superfine, M. Flavo, C. S. Johnson Jr, E. T. Sa-
mulski, R. W. Murray, J. Am. Chem. Soc. 1995, 117, 12537–
cle): NMR spectra of Pd-G
the Suzuki reaction and characterization data of the products
formed from Pd-G -catalysed reactions.
1 3 1
and Pd-G , TEM image of Pd-G after
n
12548.
[
[
27] A. Badia, S. Singh, L. Demers, L. Cuccia, G. R. Brown, R. B.
Lennox, Chem. Eur. J. 1996, 2, 359–363.
Acknowledgments
28] M. J. Hostetler, J. E. Wingate, C.-J. Zhong, J. E. Harris, R. W.
Vachet, M. R. Clark, J. D. Londono, S. J. Green, J. J. Stokes,
G. D. Wignal, G. L. Glish, M. D. Porter, N. D. Evans, R. W.
Murray, Langmuir 1998, 14, 17–30.
The authors thank the Council of Scientific and Industrial Re-
search (CSIR), Government of India and the Department of Sci-
ence and Technology (DST), Government of India (grant number
SR/S5/OC-15/2003) for financial support. V. K. R. K. thanks the
University Grants Commission (UGC) and K. S. thanks the CSIR
for research a fellowship. This article has the contribution number
NIIST-PPG-325.
[29] a) S. Mukhopadhyay, G. Rothenberg, N. Qafisheh, Y. Sasson,
Tetrahedron Lett. 2001, 42, 6117–6119; b) M. B. Thathagar, G.
Rothenberg, Org. Biomol. Chem. 2006, 4, 111–115; c) T.
Kylmälä, N. Kuuloja, Y. Xu, K. Rissanen, R. Franzén, Eur. J.
Org. Chem. 2008, 4019–4024; d) L. Zhang, L. Wang, H. Li, P.
Li, Synthesis 2008, 38, 1498–1511; e) N. Karousis, G.-E. Tsot-
sou, F. Evangelista, P. Rudolf, N. Ragoussis, N. Tagmatarchis,
J. Phys. Chem. C 2008, 112, 13463–13469; f) F. Lu, J. Ruiz, D.
Astruc, Tetrahedron Lett. 2004, 45, 9443–9445; g) Y. Uozumi,
Y. Nakai, Org. Lett. 2002, 4, 2997–3000; h) Y. M. A. Yamada,
Y. Maeda, Y. Uozumi, Org. Lett. 2006, 8, 4259–4262; i) V. Gau-
chot, W. Kroutil, A. R. Schmitzer, Chem. Eur. J. 2010, 16,
[
1] R. Shenhar, V. M. Rotello, Acc. Chem. Res. 2003, 36, 549–561.
2] L. D. Pachón, G. Rothenberg, Appl. Organomet. Chem. 2008,
[
2
2, 288–299.
3] I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009–
066.
[
[
3
6
748–6751; j) R. U. Islam, M. J. Witcomb, E. Lingen, M. S.
Scurrell, W. V. Otterlo, K. Mallick, J. Organomet. Chem. 2011,
96, 2206–2210; k) Y. Wang, J. Zhang, W. Zhang, M. Zhang,
4] M. Reetz, E. Westermann, Angew. Chem. 2000, 112, 170; An-
gew. Chem. Int. Ed. 2000, 39, 165–168.
6
[
[
5] M. T. Reetz, J. G. de Vries, Chem. Commun. 2004, 1559–1563.
6] D. Astruc, F. Lu, J. R. Aranzaes, Angew. Chem. 2005, 117,
J. Org. Chem. 2009, 74, 1923–1931; l) J. Zhang, W. Zhang, Y.
Wang, M. Zhang, Adv. Synth. Catal. 2008, 350, 2065–2076.
30] a) G. Y. Li, G. Zheng, A. F. Noonan, J. Org. Chem. 2001, 66,
8677–8681; b) G. Y. Li, J. Org. Chem. 2002, 67, 3643–3650; c)
B. Tao, D. W. Boykin, J. Org. Chem. 2004, 69, 4330–4335; d)
D. Yang, Y.-C. Chen, N.-Y. Zhu, Org. Lett. 2004, 6, 1577–1580;
e) R. A. Gossage, H. A. Jenkins, P. N. Yadav, Tetrahedron Lett.
2004, 45, 7689–7691; f) S. P. Khanapure, D. S. Garvey, Tetrahe-
dron Lett. 2004, 45, 5283–5286; g) I. D. Kostas, F. J. Andrea-
daki, D. Kovala-Demertzi, C. Prentjas, M. A. Demertzis, Tetra-
hedron Lett. 2005, 46, 1967–1970; h) J.-H. Li, Y. Liang, Y.-X.
Xie, J. Org. Chem. 2005, 70, 4393–4396; i) I. D. Kostas, B. R.
Steele, A. Terzis, S. V. Amosova, A. V. Martynov, N. A. Mak-
haeva, Eur. J. Inorg. Chem. 2006, 2642–2646; j) K. Xu, X.-Q.
Hao, J.-F. Gong, M.-P. Song, Y.-J. Wu, Aust. J. Chem. 2010,
63, 315–320.
8062; Angew. Chem. Int. Ed. 2005, 44, 7852–7872.
[
[
7] a) R. M. Crooks, M. Zhao, L. Sun, V. Chechik, L. K. Yeung,
Acc. Chem. Res. 2001, 34, 181–190; b) A. Roucoux, J. Schulz,
H. Patin, Chem. Rev. 2002, 102, 3757–3778; c) C.-C. Yang, C.-
C. Wan, Y.-Y. Wang, J. Colloid Interface Sci. 2004, 279, 433–
439; d) R. W. J. Scott, O. M. Wilson, R. M. Crooks, J. Phys.
Chem. B 2005, 109, 692–704.
8] D. H. Turkenburg, A. A. Antipov, M. B. Thathagar, G. Ro-
thenberg, G. B. Sukhorukov, E. Eiser, Phys. Chem. Chem. Phys.
[
2
005, 7, 2237–2240.
9] K. R. Gopidas, J. K. Whitesell, M. A. Fox, J. Am. Chem. Soc.
003, 125, 14168–14180.
10] K. R. Gopidas, J. K. Whitesell, M. A. Fox, J. Am. Chem. Soc.
003, 125, 6491–6502.
11] K. R. Gopidas, J. K. Whitesell, M. A. Fox, Nano Lett. 2003, 3,
757–1760.
[
[
[
[
2
2
1
[31] N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457–2483, and
12] a) M.-C. Daniel, J. Ruiz, S. Nlate, J. Palumbo, J.-C. Blais, D.
Astruc, Chem. Commun. 2001, 2000–2001; b) M.-C. Daniel, J.
Ruiz, S. Nlate, J.-C. Blais, D. Astruc, J. Am. Chem. Soc. 2003,
references cited therein.
[32] Y. Li, X. M. Hong, D. M. Collard, M. A. El-Sayed, Org. Lett.
2000, 2, 2385–2388.
[33] T. Mizoroki, K. Mori, A. Ozaki, Bull. Chem. Soc. Jpn. 1971,
125, 2617–2628.
[13] Y.-S. Shon, D. Choi, Curr. Nanosci. 2007, 3, 245–254.
44, 581.
Eur. J. Org. Chem. 2012, 3447–3458
© 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
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