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Volume 220, 2019
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Suzuki–Miyaura coupling revisited: an integrated computational study

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Abstract

New density functional theory (DFT) computations are reported concerning the mechanism of the Suzuki–Miyaura cross-coupling reaction of aryl halides and aryl boronic acids catalyzed by palladium phosphine complexes. The calculations are aimed at refining the understanding of the overall catalytic mechanism using state of the art theoretical approaches (including, for the first time, an attempt to describe the Gibbs energy of the reactant base in a realistic way). New experimental results (Thomas and Denmark, Science, 2016, 352, 329–332) concerning pre-transmetallation intermediates with a Pd–O–B linkage provide an invaluable benchmark to test the accuracy of the calculations. The calculations show that bottlenecks to catalysis associated with oxidative addition, X-to-O substitution at Pd, and transmetallation can lie close in energy.

Graphical abstract: Suzuki–Miyaura coupling revisited: an integrated computational study

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Submitted
25 Apr 2019
Accepted
04 Jun 2019
First published
07 Jun 2019

Faraday Discuss., 2019,220, 425-442
Article type
Paper

Suzuki–Miyaura coupling revisited: an integrated computational study

T. Yaman and J. N. Harvey, Faraday Discuss., 2019, 220, 425
DOI: 10.1039/C9FD00051H

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