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804452

Sigma-Aldrich

Potassium 3-ethoxycarbonylbenzoyltrifluoroborate

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About This Item

Formula empirica (notazione di Hill):
C10H9BF3KO3
Numero CAS:
1622923-42-5
Peso molecolare:
284.08
Codice UNSPSC:
12352103
ID PubChem:
329768873
NACRES:
NA.22

Forma fisica

powder

Stringa SMILE

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;;
WJLIBYVPNAKYHP-UHFFFAOYSA-N

Applicazioni

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.

Altre note

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

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319,H335

Classi di pericolo

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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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
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
Andrea M Hardman et al.
Organic & biomolecular chemistry, 11(35), 5793-5797 (2013-08-03)
Highly functionalized oxazinanes are efficiently prepared through urea-catalyzed formal [3 + 3] cycloaddition reactions of nitrones and nitrocyclopropane carboxylates. The reaction system is general with respect to both the nitrocyclopropane carboxylates and nitrones enabling the preparation of a large family
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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