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Merck
CN

790397

Potassium 2-bromo-4-(trifluoromethyl)pyridine-3-trifluoroborate

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经验公式(希尔记法):
C6H2BBrF6KN
分子量:
331.89
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
Assay:
97%
Form:
solid
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InChI

1S/C6H2BBrF6N.K/c8-5-4(7(12,13)14)3(1-2-15-5)6(9,10)11;/h1-2H;/q-1;+1

SMILES string

BrC1=C([B-](F)(F)F)C(C(F)(F)F)=CC=N1.[K+]

InChI key

WGDRKFJAJWNHQI-UHFFFAOYSA-N

assay

97%

form

solid

Application

An organotrifluoroborate involved in:
  • Nickel-catalyzed cross-coupling reactions and C-O activation
  • Suzuki cross-coupling,
  • Copper-catalyzed cross-coupling reactions
  • Stereoselective Mukaiyama aldol reactions

Organotrifluoroborates as versatile and stable boronic acid surrogates.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

法规信息

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Copper catalyzed cross-coupling reactions of diaryl ditellurides with potassium aryltrifluoroborate salts
Journal of the Brazilian Chemical Society, 20, 988-992 (2009)
J Michael Ellis et al.
The Journal of organic chemistry, 73(22), 9151-9154 (2008-10-16)
A new synthesis of 3,3'-bioxindoles is reported that is well suited for the preparation of unsymmetrical structures. In the key step, 3-hydroxy-3,3'-bioxindoles are constructed by Mukaiyama aldol reaction of 2-siloxyindoles with isatins. These tertiary carbinols are formed in high diastereoselectivities
Synthesis of 5-aryl- and 5-heteroaryl-7-carboxyl-8-hydroxyquinaldines through Suzuki cross-coupling reaction with potassium organotrifluoroborates
Synthesis, 4, 619-630 (2010)
Gary A Molander et al.
Organic letters, 12(18), 4022-4025 (2010-08-19)
A general method based on nickel-catalyzed C-O activation of various phenol derivatives with potassium (hetero)aryltrifluoroborates has been developed. A large number of heterobiaryls can be easily obtained with yields up to 99% using methanesulfonate cross-coupling partners.
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

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