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Is oxidative addition indeed the rate-determining step of the Suzuki–Miyaura reaction with less-reactive aryl chlorides under 'ligand-free' conditions?
- Source :
- Journal of Organometallic Chemistry. 929:121571
- Publication Year :
- 2020
- Publisher :
- Elsevier BV, 2020.
-
Abstract
- The retarded oxidative addition of aryl chloride to Pd(0) is believed, by most scientists, to be the main hindrance in achieving effective conversion in the Suzuki–Miyaura reaction and other cross-coupling reactions of aryl chlorides. Herein, we have demonstrated by competing experiments, using two aryl chlorides under “ligand-free” catalytic conditions (absence of strong ligands; high ratio of substrate to catalyst), that the elementary step of oxidative addition is substantially reversible. This implies that the hypothesis on the rate-determining character of the oxidative addition step is incorrect, and the existing problems with aryl chloride conversion in the Suzuki–Miyaura reaction are caused by some other reasons that need to be investigated.
- Subjects :
- 010405 organic chemistry
Ligand
Aryl
Organic Chemistry
Substrate (chemistry)
010402 general chemistry
Rate-determining step
01 natural sciences
Biochemistry
Combinatorial chemistry
Oxidative addition
Chloride
0104 chemical sciences
Catalysis
Inorganic Chemistry
chemistry.chemical_compound
chemistry
Materials Chemistry
medicine
Physical and Theoretical Chemistry
High ratio
medicine.drug
Subjects
Details
- ISSN :
- 0022328X
- Volume :
- 929
- Database :
- OpenAIRE
- Journal :
- Journal of Organometallic Chemistry
- Accession number :
- edsair.doi...........9986cc49646c6da23e2c2ab1a4f56a02
- Full Text :
- https://doi.org/10.1016/j.jorganchem.2020.121571