4
7
reduced by SAINT and corrected for absorption effects by the
Brink, I. W. C. E. Arends, M. Hoogenraad, G. Verspui and
R. A. Sheldon, Adv. Synth. Catal., 2003, 345, 497–505.
6 D. R. Jensen, J. S. Pugsley and M. S. Sigman, J. Am. Chem. Soc., 2001,
4
8
multi-scan method (SADABS). The structure was solved by
direct methods (SIR-2002) and refined against all F data by
1
4
9
2
1
23, 7475–7476.
17 E. M. Ferreira and B. M. Stoltz, J. Am. Chem. Soc., 2001, 123,
725–7726.
5
0
full-matrix least-squares techniques (SHELXTL-6.12) mini-
2
2 2
7
mizing w[F0 − F ] . All non-hydrogen atoms were included in
c
1
1
2
2
2
2
8 D. R. Jensen, M. J. Schulz, J. A. Mueller and M. S. Sigman, Angew.
Chem., Int. Ed., 2003, 42, 3810–3813.
9 S. Paavola, K. Zatterberg, T. Privalov, I. Csöregh and C. Moberg, Adv.
Synth. Catal., 2004, 346, 237–244.
0 G. Urgoitia, R. SanMartin, M. T. Herrero and E. Domínguez, Green
Chem., 2011, 13, 2161–2166.
1 D. M. Pearson, N. R. Conley and R. M. Waymouth, Organometallics,
2011, 30, 1445–1453.
2 G. J. ten Brink, I. W. C. E. Arends and R. A. Sheldon, Adv. Synth. Catal.,
2002, 344, 355–369.
3 B. A. Steinhoff and S. S. Stahl, J. Am. Chem. Soc., 2006, 128,
4348–4355.
calculated positions and refined with anisotropic thermal para-
meters. Hydrogen atoms were included in calculated positions
and allowed to ride on their respective attached carbon atoms
with the isotropic temperature factors (Uiso values) fixed at 1.2
times (1.5 times for the methyl groups) those Ueq values of the
corresponding atoms. 1-Py: C H N O Pd, M = 440.81, mono-
2
1 22 2 2
clinic, a = 11.3433(13) Å, b = 14.1759(16) Å, c = 13.0253(15)
Å, α = 90.00°, β = 111.398(3)°, γ = 90.00°, V = 1950.1(4) Å ,
3
T = 173(2) K, space group, P21/n, Z = 4, μ(MoK ) =
α
1
0
.968 mm− , 18 782 reflections measured, 3394 independent
24 (a) R. M. Trend and B. M. Stoltz, J. Am. Chem. Soc., 2004, 126, 4482–
483; (b) R. M. Trend and B. M. Stoltz, J. Am. Chem. Soc., 2008, 130,
4
reflections (Rint = 0.0570). The final R values were 0.0339
I > 2σ(I)). The final wR(F ) values were 0.0891 (all data). The
goodness of fit on F was 1.010. CCDC reference number
92325 contains the supplementary crystallographic data for this
1
2
15957–15966; (c) D. C. Ebner, J. T. Bagdanoff, E. M. Ferreira,
R. M. McFadden, D. C. Caspi, R. M. Trend and B. M. Stoltz, Chem.–
Eur. J., 2009, 47, 12978–12992.
(
2
8
25 T. Privalov, C. Linde, K. Zatterberg and C. Moberg, Organometallics,
2005, 24, 885–893.
paper.
2
6 (a) S. S. Stahl, J. L. Thorman, R. C. Nelson and M. A. Kozee, J. Am.
Chem. Soc., 2001, 123, 7188–7189; (b) M. M. Konnick, I. A. Guzel and
S. S. Stahl, J. Am. Chem. Soc., 2004, 126, 10212–10213; (c) B. V. Popp,
J. E. Wendlandt, C. R. Landis and S. S. Stahl, Angew. Chem. Int. Ed.,
Acknowledgements
2
007, 46, 601–604.
This work was supported by the Government of Spain (project
CTQ2009-11721), Junta de Andalucía (project FQM6276), and
European Union (FEDER funds). C. M. thanks a postdoctoral
research contract from the Junta de Andalucía. O. Sh. also
thanks the Council of Grants of the President of the Russian
Federation for young scientists (project MK-966.2012.3).
2
7 (a) J. M. Keith, R. J. Nielsen, J. Oxgaard and W. A. Goddard, J. Am.
Chem. Soc., 2005, 127, 13172–13179; (b) M. C. Denney, N. A. Smythe,
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1
28, 2508–2509; (c) J. M. Keith, R. P. Muller, R. A. Kemp,
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2009, 131, 1416–1425.
2
8 (a) B. V. Popp and S. S. Stahl, J. Am. Chem. Soc., 2007, 129,
4
2
410–4422; (b) B. V. Popp and S. S. Stahl, Chem.–Eur. J., 2009, 15,
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Dalton Trans., 2012, 41, 14087–14100 | 14099