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/168
167
˚
0.71073 A)
monochromatized MoÁ
/
Ka radiation (lꢀ
/
References
using variable v-scan technique.
[1] Y.C. Neo, J.J. Vittal, T.S.A. Hor, J. Chem. Soc. Dalton Trans.
(2002) 337.
Two standard reflections were monitored after every
125 data measurements, showing only small random
variations. The raw data were processed with the learnt-
profile procedure [48], and absorption corrections were
applied by fitting a pseudo-ellipsoid to the c-scan data
of selected strong reflections over a range of 2u angles
[49]. The structures were solved with the Patterson
superposition method with the aid of subsequent
difference Fourier syntheses. The CF3 groups in the I
are disordered. All the non-hydrogen atoms were refined
[2] C. Oldham, in: G. Wilkinson, R.D. Gillard, J.A. McCleverty
(Eds.), Comprehensive Coordination Chemistry, vol. 2 (Ch. 15.6),
Pergamon Press, Oxford, 1987, p. 435.
[3] (a) J. Tsuji, Organic Synthesis with Palladium Compounds,
Springer-Verlag, New York, 1980;
(b) P.M. Maitlis, The Organic Chemistry of Palladium, Catalytic
Reactions, vol. II, Academic Press, New York, 1971;
(c) N. Miyaura, A. Suzuki, Chem. Rev. 95 (1995) 2457;
(d) K.S. Gan, T.S.A. Hor, in: A. Togni, T. Hayashi (Eds.),
Ferrocenes-Homogeneous Catalysis, Organic Synthesis and Ma-
terials Science (Ch. 1), VCH, Weinheim, 1995, p. 3;
(e) P.N. Rylander, Catalytic Hydrogenation Over Platinum
Metals, Academic Press, New York and London, 1967;
(f) A. Yamamoto, Organotransition Metal Chemistry, Wiley,
New York, 1986;
anisotropically. Hydrogen atoms of the organic ligands
˚
were generated geometrically (CÃ
/
Hꢀ0.95 A), assigned
/
appropriate isotropic thermal parameters, and allowed
to ride on their parent carbon atoms. The phenyl groups
on the phosphine were treated as rigid groups. The other
non-hydrogen atoms were refined anisotropically, and
the hydrogen atoms of the cyclopentadienyl groups were
included in the structure-factor calculations with as-
signed isotropic temperature factors. All computations
were performed with the SHELXTL-PC program package
[50]. Analytical expressions of neutral-atom scattering
factors were employed, and anomalous-dispersion cor-
rections were incorporated [51].
(g) W. Cabri, I. Candiani, A. Bedeschi, J. Org. Chem. 57 (1992)
3558;
(h) L. Xu, W. Chen, J. Xiao, Organometallics 19 (2000) 1123;
(i) I.P. Beletskaya, A.V. Cheprakov, Chem. Rev. 100 (2000) 3009.
[4] (a) B. Ramesh, D.T. Sadanand, S.G. Reddy, K.V. Swamy, P.K.
Saiprakash, Trans. Met. Chem. 25 (2000) 639;
(b) Y. Miki, H. Shirokoshi, K. Matsushita, Tetrahedron Lett. 40
(1999) 4347;
(c) A. Seayad, A.A. Kelkar, R.V. Chaudhari, Ind. Eng. Chem.
Res. 37 (1998) 2180;
(d) E. Drent, J.A.M.V. v. Broekhoven, M.J. Doyle, J. Organomet.
Chem. 417 (1991) 235.
¨
[5] W.A. Hermann, C. Brossmer, K. .Ofele, C. Reisinger, T.
The relevant crystallographic data and refinement
details of all complexes are shown in Table 3.
Priermeier, M. Beller, H. Fischer, Angew. Chem. Int. Ed. Engl.
34 (17) (1995) 1844.
[6] F. Ozawa, A. Kubo, T. Hayashi, Chem. Lett. (1992) 2177.
[7] J.W. Han, T. Hayashi, Tetrahedron Asymm. 13 (2002) 325.
[8] A.Y. Lebedev, V.V. Izmer, D.N. Kazyul’kin, I.P. Beletskaya,
A.Z. Voskoboynikov, Org. Lett. 4 (2002) 623.
[9] T. Harayama, T. Akiyama, Y. Nakano, K. Shibaike, H.
Akamatsu, A. Hori, H. Abe, Y. Takeuchi, Synthesis-Stuttgart
(2002) 237.
4. Supplementary materials
The ORTEP plots of complex I, III, IV and
PdBr2(dppf) are available as supplementary materials.
Crystallographic data (CIF files) for the structural
analysis have been deposited with the Cambridge
[10] A. Schnyder, A.F. Indolese, J. Org. Chem. 67 (2002) 594.
[11] G.R. Cairns, R.J. Cross, D. Stirling, J. Mol. Catal. A Chem. 172
(2001) 207.
Crystallographic Data Centre, CCDC no. 169371Á
/
169376 for the six structures [I, III, IV, VIII, X and
PdBr2(dppf)]. Copies of this information may be ob-
tained free of charge from The Director, CCDC, 12
[12] (a) C. Amatore, A. Jutand, M.A. M’Barki, Organometallics 11
(1992) 3009;
(b) C. Amatore, E. Carre´, A. Jutand, M.A. M’Barki, Organome-
tallics 14 (1995) 1818;
Union Road, Cambridge CB2 1EZ, UK (Fax: ꢂ44-
/
(c) C. Amatore, E. Carre´, A. Jutand, M.A. M’Barki, G. Meyer,
Organometallics 14 (1995) 5605;
1223-336033; e-mail: deposit@ccdc.cam.ac.uk or www:
(d) C. Amatore, A. Jutand, J. Organomet. Chem. 576 (1999) 254;
(e) C. Amatore, A. Jutand, Acc. Chem. Res. 33 (2000) 314.
[13] T.A. Stephenson, S.M. Morehouse, A.R. Powell, J.P. Heffer, G.
Wilkinson, J. Chem. Soc. (1965) 3632.
[14] T.R. Jack, J. Powell, Can. J. Chem. 53 (1975) 2558.
[15] T.A. Stephenson, G. Wilkinson, J. Inorg. Nucl. Chem. 29 (1967)
2122.
Acknowledgements
We acknowledge the National University of Singa-
pore for financial support (R143-000-053-112) and
technical assistance from the Chemistry Department.
We thank G.K. Tan for assistance in X-ray analysis.
Y.C. Neo, J.S.L. Yeo and P.M.N. Low are grateful to
NUS for a research scholarship. T.C.W. Mak acknowl-
edges support from the Hong Kong Research Grants
Council, Earmarked Grant Number CUHK 4022/98P.
[16] J.E. Macintyre, F.M. Daniel, V.M. Stirling, Dictionary of
Inorganic Compounds, vol. 2, Chapman & Hall, London, 1992,
p. 2421.
[17] S.A. Aucott, A.M.Z. Slawin, J.D. Woollins, Polyhedron 19 (2000)
499.
[18] W.P. Su, R. Cao, M. Hong, D. Wu, J. Lu, J. Chem. Soc. Dalton
Trans. (2000) 1527.
[19] C. Bird, R.L. Booth, R.N. Haszeldine, G.R.H. Neuss, M.A.
Smith, A. Flood, J. Chem. Soc. Dalton Trans. (1982) 1109.