10.1002/adsc.201700840
Advanced Synthesis & Catalysis
Computational Details
Strassert, F. Glorius, Angew. Chem. Int. Ed. 2015, 54,
4508-4511; f) M. R. Fructos, M. M. Díaz-Requejo, P. J.
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Conde, G. Sabenya, M. Rodríguez, V. Postils, J. M. Luis,
M. M. Díaz-Requejo, M. Costas, P. J. Pérez, Angew.
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All the calculations reported in this paper were performed
with the Gaussian 09 suite of programs.[22] Electron
correlation was partially taken into account using the hybrid
functional usually denoted as B3LYP[23] in conjunction with
the D3 dispersion correction suggested by Grimme et al.[24]
using the double-quality plus polarization def2-SVP[25]
basis set for all atoms. Reactants and products were
characterized by frequency calculations,[26] and have
positive definite Hessian matrices. Transition structures
(TS’s) show only one negative eigenvalue in their
diagonalized force constant matrices, and their associated
eigenvectors were confirmed to correspond to the motion
along the reaction coordinate under consideration using the
Intrinsic Reaction Coordinate (IRC) method.[27] Solvents
effects were also taken into account using the Polarizable
Continuum Model (PCM)[28] during the geometry
optimizations. This level is denoted PCM-(CHCl3)-B3LYP-
D3/def2-SVP. Single-point energy refinements were carried
out at the M06L[29,30]/def2-TZVPP[25] level of theory
employing the PCM model to account for solvation. This
level is denoted PCM(CHCl3)-M06L/def2-TZVPP//PCM-
(CHCl3)-B3LYP-D3/def2-SVP.
[4] H. M. L. Davies, B. T. Parr, in Contemporary Carbene
Chemistry; Wiley: Hoboken, NJ, 2013, pp 363-403.
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Supporting Information
[7] a) D. F. Taber, J. C. Amedio Jr., R. G. Sherill, J. Org.
Chem. 1986, 51, 3382-3384; b) M. L. Rosenberg, J. H.
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Detailed experimental procedures, characterization data and
copies of NMR spectra for all new compounds, Figure S1,
as well as Cartesian coordinates of all species described in
the text are available in the Supporting Information.
[8] D. Solé, F. Mariani, M.-L. Bennasar, I. Fernández,
Angew. Chem. Int. Ed. 2016, 55, 6467-6470.
Acknowledgements
[9] For the intramolecular Pd-catalysed CAr(sp2)–H
insertion of -diazo--(methoxycarbonyl)acetanilides
to afford oxindoles, see: D. Solé, F. Pérez-Janer, I.
Fernández, Chem. Commun. 2017, 53, 3110-3113.
The authors gratefully acknowledge financial support for this work
from the Spanish Ministerio de Economía y Competitividad,
Fondos Europeos para el Desarrollo Regional (MINECO-
FEDER) (projects CTQ2013-44303-P, CTQ2014-51912-REDC,
CTQ2015-64937-R and CTQ2016-78205-P).
[10] For selected examples on catalyst-controlled
selectivities using a broader set of catalysts, see: a) B.
Ma, F.-L. Chen, X.-Y. Xu, Y.-N. Zhang, L.-H. Hu, Adv.
Synth. Catal. 2014, 356, 416-420; b) Y. Deng, C. Jing,
H. Arman, M. P. Doyle, Organometallics 2016, 35,
3413-3420.
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10
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