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804452

Sigma-Aldrich

Potassium 3-ethoxycarbonylbenzoyltrifluoroborate

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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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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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
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, 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
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

Related Content

The Bode Group aims to develop new reactions and reagents for the synthesis of complex molecules. The Bode Group has developed N-mesityl-substituted NHCs as organocatalysts for the catalytic generation of reactive species including activated carboxylates, homoenolates, and enolates. These novel catalysts and reactions have made possible a new generation of highly enantioselective annulations from simple starting materials under mild reaction conditions, usually at room temperature and without added reagents. Furthering the goal of designing new reagents to enable the assembly of complex molecules, the Bode group has developed SnAP reagents for the facile, one-pot conversion of aldehydes into N-unprotected, saturated N-heterocycles, including bicyclic and spirocyclic structures. These easy to handle reagents provide a simple and robust alternative to the challenging and restrictive cross-coupling methods for the functionalization of saturated N-heterocycles.

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