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Suzuki-Miyaura coupling revisited: an integrated computational study
- Source :
- Faraday discussions. 220
- Publication Year :
- 2019
-
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. ispartof: FARADAY DISCUSSIONS vol:220 issue:0 pages:425-442 ispartof: location:England status: published
- Subjects :
- MECHANISM
Materials science
ARYL HALIDES
BORONIC ACID
chemistry.chemical_element
02 engineering and technology
010402 general chemistry
01 natural sciences
Catalysis
chemistry.chemical_compound
symbols.namesake
Transmetalation
Computational chemistry
OXIDATIVE ADDITION
Physical and Theoretical Chemistry
TRANSMETALATION PROCESS
Science & Technology
Chemistry, Physical
PALLADIUM
Aryl
FREE-ENERGY
FORMING REDUCTIVE ELIMINATION
021001 nanoscience & nanotechnology
Oxidative addition
REACTIVITY
0104 chemical sciences
Gibbs free energy
Chemistry
chemistry
Physical Sciences
symbols
COMPLEXES
Density functional theory
0210 nano-technology
Phosphine
Palladium
Subjects
Details
- ISSN :
- 13645498
- Volume :
- 220
- Database :
- OpenAIRE
- Journal :
- Faraday discussions
- Accession number :
- edsair.doi.dedup.....a65bff6c165510e6d0d0e2a0c94e47f4