804452
Potassium 3-ethoxycarbonylbenzoyltrifluoroborate
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About This Item
Empirical Formula (Hill Notation):
C10H9BF3KO3
CAS Number:
Molecular Weight:
284.08
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
form
powder
SMILES string
CCOC(C1=CC=CC(C(B(F)(F)F)=O)=C1)=O.[K]
InChI
1S/C10H9BF3O3.K.H/c1-2-17-10(16)8-5-3-4-7(6-8)9(15)11(12,13)14;;/h3-6H,2H2,1H3;;
InChI key
WJLIBYVPNAKYHP-UHFFFAOYSA-N
Application
Acyltrifluroborates (KAT′s) are bench, air, and moisture stable reagents for rapid, chemoselective amide bond formations with hydroxylamines. These amide bond forming reactions proceed under aqueous conditions, without the need for coupling reagents or protecting groups. This product was introduced in collaboration with the Bode Research Group.
Other Notes
Rapid Ligations with Equimolar Reactants in Water with the Potassium Acyltrifluoroborate (KAT) Amide Formation
Amide-Forming Ligation of Acyltrifluoroborates and Hydroxylamines in Water
Synthesis of Chemically and Configurationally Stable Monofluoro Acylboronates: Effect of Ligand Structure on their Formation, Properties, and Reactivities
Amide-Forming Ligation of Acyltrifluoroborates and Hydroxylamines in Water
Synthesis of Chemically and Configurationally Stable Monofluoro Acylboronates: Effect of Ligand Structure on their Formation, Properties, and Reactivities
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
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David M Nickerson et al.
Chemical communications (Cambridge, England), 49(39), 4289-4291 (2012-12-01)
The strategic incorporation of internal Lewis acids onto urea scaffolds gives rise to a family of tunable hydrogen bond donor catalysts. The nature of the Lewis acid and associated ligands affects the urea polarization, acidity, and activity in reactions of
Sonia S So et al.
Organic letters, 14(2), 444-447 (2012-01-03)
Boronate ureas operate as catalysts for the activation of nitrocyclopropane carboxylates in nucleophilic ring-opening reactions. A variety of amines were found to open the urea-activated nitrocyclopropane carboxylates, generating highly useful nitro ester building blocks in good yields. Standard manipulations allow
Tyler J Auvil et al.
Angewandte Chemie (International ed. in English), 52(43), 11317-11320 (2013-09-17)
It takes two: A unique organocatalyzed cascade for the unsymmetric double arylation of α-nitrodiazoesters is described. This organocascade features the strategic use of carbene-activating anilines in conjunction with a urea catalyst, thus allowing for the synthesis of pharmaceutically attractive α-diarylesters
Sonia S So et al.
The Journal of organic chemistry, 79(11), 4832-4842 (2014-05-07)
The power of hydrogen-bond donor catalysis has been harnessed to elicit and control carbene-like reactivity from nitrodiazoesters. Specifically, select ureas have been identified as effective catalysts for N-H insertion and multicomponent coupling reactions of nitrodiazoesters, anilines, and aromatic nucleophiles, thereby
Sonia S So et al.
Organic letters, 13(4), 716-719 (2011-01-14)
Boronate ureas are introduced as a new class of noncovalent catalysts for conjugate addition reactions with enhanced activity. Through intramolecular coordination of the urea functionality to a strategically placed Lewis acid, rate enhancements up to 10 times that of more
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