739588
Potassium 2-methoxypyrimidin-5-yl-5-trifluoroborate
90%
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About This Item
Empirical Formula (Hill Notation):
C5H5BF3KN2O
CAS Number:
Molecular Weight:
216.01
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
Assay
90%
form
solid
mp
239-254 °C
SMILES string
[K+].COc1ncc(cn1)[B-](F)(F)F
InChI
1S/C5H5BF3N2O.K/c1-12-5-10-2-4(3-11-5)6(7,8)9;/h2-3H,1H3;/q-1;+1
InChI key
ACPITJHSWGPRRF-UHFFFAOYSA-N
Application
Potassium 2-methoxypyrimidin-5-yl-5-trifluoroborate can be used as a substrate in:
- Metal-free synthesis of biaryls through oxidative electrocoupling reaction.
- Cross-coupling reactions with unactivated alkyl halides in the presence of a nickel catalyst.
- Suzuki-Miyaura coupling with aryl and heteroaryl halides using a palladium catalyst.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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Nickel-catalyzed cross-coupling of potassium aryl-and heteroaryltrifluoroborates with unactivated alkyl halides
Molander GA, et al.
Organic Letters, 12(24), 5783-5785 (2010)
Arif Music et al.
Journal of the American Chemical Society, 142(9), 4341-4348 (2020-02-11)
We report herein versatile, transition metal-free and additive-free (hetero)aryl-aryl coupling reactions promoted by the oxidative electrocoupling of unsymmetrical tetra(hetero)arylborates (TABs) prepared from ligand-exchange reactions on potassium trifluoroarylborates. Exploiting the power of electrochemical oxidations, this method complements the existing organoboron toolbox.
Electrochemical Synthesis of Biaryls via Oxidative Intramolecular Coupling of Tetra(hetero)arylborates
Music A, et al.
Journal of the American Chemical Society, 142(9), 4341-4348 (2020)
Gary A Molander et al.
The Journal of organic chemistry, 74(3), 973-980 (2008-12-25)
A wide variety of bench-stable potassium heteroaryltrifluoroborates were prepared, and general reaction conditions were developed for their cross-coupling to aryl and heteroaryl halides. The cross-coupled products were obtained in good to excellent yields. This method represents an efficient and facile
Scope of the Suzuki- Miyaura cross-coupling reactions of potassium heteroaryltrifluoroborates
Molander GA, et al.
The Journal of Organic Chemistry, 74(3), 973-980 (2009)
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