Orthogonal Selectivities under
Pd(0) Catalysis with Solvent Polarity: An Interplay of
Computational and Experimental Studies

Fabien Proutiere; Franziska Schoenebeck

doi:10.1055/s-0031-1290564

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Synlett 2012(5): 645-648
DOI: 10.1055/s-0031-1290564

SYNPACTS

Orthogonal Selectivities under Pd(0) Catalysis with Solvent Polarity: An Interplay of Computational and Experimental Studies

Fabien Proutiere, Franziska Schoenebeck*
Laboratory for Organic Chemistry, Swiss Federal Institute of Technology ETH Zürich, Wolfgang-Pauli-Str. 10, 8093 Zürich, Switzerland
e-Mail: schoenebeck@org.chem.ethz.ch;

Further Information

Publication History

Received 2 November 2011
Publication Date:
24 February 2012 (online)

Abstract
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Abstract

We recently communicated a combined computational and experimental study of our discovery of selectivity reversal in Pd cross-coupling in polar solvent for a competition reaction of C-Cl vs. C-OTf functionalization. Our data suggested that the reactivity in polar solvent is consistent with anionic Pd(0) and in nonpolar solvent with neutral Pd(0) catalysis. This article will discuss the power and limits of current computational approaches to explore mechanisms in the context of this study and will highlight the use of experiments in parallel to computational approaches to test theoretical conclusions and aid theoretical analyses.

Key words

DFT - cross-coupling - anionic palladium - Suzuki coupling - solvent

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