Tetrabutylammonium 2-pyridyltriolborate salts for Suzuki-Miyaura cross-coupling reactions with aryl chlorides.

Tetrabutylammonium 2-pyridyltriolborate salts for Suzuki-Miyaura cross-coupling reactions with aryl chlorides.

Organic letters (2013-08-21)

Shohei Sakashita, Miho Takizawa, Juugaku Sugai, Hajime Ito, Yasunori Yamamoto

RÉSUMÉ

Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of tetrabutylammonium 2-pyridyltriolborate salts with various aryl (heteroaryl) chlorides can produce the corresponding desired coupling products with good to excellent yields. These tetrabutylammonium salts are more reactive than the corresponding lithium salts. The coupling reactions with aryl chlorides progressed in the presence of PdCl2dcpp (3 mol %) and CuI/MeNHCH2CH2OH (20 mol %) in anhydrous DMF without bases.

MATÉRIAUX

Référence du produit

Marque

Description du produit

268100

Sigma-Aldrich

Phosphate de tétrabutylammonium monobasique solution, 1.0 M in H₂O

216143

Sigma-Aldrich

Fluorure de tétrabutylammonium solution, 1.0 M in THF

86870

Sigma-Aldrich

Tetrabutylammonium chloride, ≥97.0% (NT)

178780

Sigma-Aldrich

Tetrabutylammonium hydroxide solution, 40 wt. % in H₂O

140775

Sigma-Aldrich

Iodure de tétrabutylammonium, reagent grade, 98%

230189

Sigma-Aldrich

Tetrabutylammonium hydroxide solution, 1.0 M in methanol

86885

Sigma-Aldrich

Tetrabutylammonium perchlorate, ≥95.0% (T)

155837

Sigma-Aldrich

Tetrabutylammonium hydrogensulfate, 97%

86854

Supelco

Tetrabutylammonium hydroxide solution, ~40% in water, suitable for ion chromatography

358665

Sigma-Aldrich

Tetrabutylammonium cyanide, 95%

426288

Sigma-Aldrich

Tetrabutylammonium bromide, ACS reagent, ≥98.0%

86868

Sigma-Aldrich

Bisulfate de tétrabutylammonium, puriss., ≥99.0% (T)

359173

Sigma-Aldrich

Tetrabutylammonium nitrate, 97%

86890

Sigma-Aldrich

Iodure de tétrabutylammonium, ≥99.0% (AT)

651664

Sigma-Aldrich

Tetrabutylammonium azide

86833

Sigma-Aldrich

Phosphate de tétrabutylammonium monobasic, puriss., 99% (T)

193119

Sigma-Aldrich

Tetrabutylammonium bromide, ReagentPlus^®, ≥99.0%

361399

Sigma-Aldrich

Fluorure de tétrabutylammonium solution, 75 wt. % in H₂O

86853

Supelco

Bisulfate de tétrabutylammonium, suitable for ion pair chromatography, LiChropur^™, ≥99.0%

86893

Supelco

Tetrabutylammonium perchlorate, for electrochemical analysis, ≥99.0%

86880

Sigma-Aldrich

Tetrabutylammonium hydroxide solution, technical, ~40% in H₂O (~1.5 M)

462144

Sigma-Aldrich

Tetrabutylammonium bromide solution, 50 wt. % in H₂O

86857

Supelco

Tetrabutylammonium bromide, suitable for ion pair chromatography, LiChropur^™, ≥99.0%

86863

Sigma-Aldrich

Tetrabutylammonium hydroxide solution, 53.5-56.5% in H₂O

72453

Sigma-Aldrich

Tetrabutylammonium bisulfate solution, ~55% in H₂O

79989

Sigma-Aldrich

Tetrabutylammonium cyanide, technical, ≥80%

86852

Supelco

Tetrabutylammonium chloride, suitable for ion pair chromatography, LiChropur^™, ≥99.0%

98479

Supelco

Tetrabutylammonium bisulfate solution, suitable for ion pair chromatography, LiChropur^™, concentrate, ampule

86903

Supelco

Iodure de tétrabutylammonium, suitable for ion pair chromatography, LiChropur^™, ≥99.0%