Journal of Computational Chemistry
Journal of Computational Chemistry
5 years ago

Theoretical study on selectivity trends in (N-heterocyclic carbene)-Pd catalyzed mizoroki–heck reactions: Exploring density functionals methods and molecular models

Theoretical study on selectivity trends in (N-heterocyclic carbene)-Pd catalyzed mizoroki–heck reactions: Exploring density functionals methods and molecular models
Oscar Navarro, Ataualpa A. C. Braga, Ana Paula de Lima Batista, Vitor H. Menezes da Silva
The regioselectivity of the NHC-Pd catalyzed Heck coupling reaction between phenyl bromide and styrene has been investigated using the density functional theory, wave-function (WF)-based methods and two different sizes of model ligands. In addition to the WF methods, the TPSS-D3, ω B97X-D, BP86-D3, and M06-L density functionals were reliable approaches to be applied, independently of the basis set. Moreover, the NCI analysis showed that weak interactions are important forces to be taken into account when exploring the regioselectivity of this reaction, mainly when a crowded NHC ligand is present. © 2017 Wiley Periodicals, Inc. To predict the regioselectivity of the NHC-Pd catalyzed Heck coupling reaction involving phenyl bromide and styrene, small and large N-heterocyclic carbene (NHC) ligands were modeled using several density functionals and wave-function (WF)-based methods. In addition to the WF methods, the TPSS-D3, ω B97X-D, BP86-D3, and M06-L density functionals were reliable density functional approaches to predict the experimental regioselectivity trends when bulky NHC ligands were the target.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/jcc.24867

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