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

ABSTRACT

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.

MATERIALS

Product Number

Brand

Product Description

79989

Sigma-Aldrich

Tetrabutylammonium cyanide, technical, ≥80%

86854

Supelco

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

358665

Sigma-Aldrich

Tetrabutylammonium cyanide, 95%

86893

Supelco

Tetrabutylammonium perchlorate, for electrochemical analysis, ≥99.0%

86880

Sigma-Aldrich

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

86863

Sigma-Aldrich

Tetrabutylammonium hydroxide solution, 53.5-56.5% in H₂O

86885

Sigma-Aldrich

Tetrabutylammonium perchlorate, ≥95.0% (T)

178780

Sigma-Aldrich

Tetrabutylammonium hydroxide solution, 40 wt. % in H₂O

268100

Sigma-Aldrich

Tetrabutylammonium phosphate monobasic solution, 1.0 M in H₂O

155837

Sigma-Aldrich

Tetrabutylammonium hydrogensulfate, 97%

230189

Sigma-Aldrich

Tetrabutylammonium hydroxide solution, 1.0 M in methanol

86870

Sigma-Aldrich

Tetrabutylammonium chloride, ≥97.0% (NT)

86833

Sigma-Aldrich

Tetrabutylammonium phosphate monobasic, puriss., 99% (T)

86857

Supelco

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

86852

Supelco

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

86890

Sigma-Aldrich

Tetrabutylammonium iodide, ≥99.0% (AT)

72453

Sigma-Aldrich

Tetrabutylammonium bisulfate solution, ~55% in H₂O

359173

Sigma-Aldrich

Tetrabutylammonium nitrate, 97%

98479

Supelco

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

140775

Sigma-Aldrich

Tetrabutylammonium iodide, reagent grade, 98%

462144

Sigma-Aldrich

Tetrabutylammonium bromide solution, 50 wt. % in H₂O

86853

Supelco

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

86903

Supelco

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

86868

Sigma-Aldrich

Tetrabutylammonium bisulfate, puriss., ≥99.0% (T)

651664

Sigma-Aldrich

Tetrabutylammonium azide

361399

Sigma-Aldrich

Tetrabutylammonium fluoride solution, 75 wt. % in H₂O

426288

Sigma-Aldrich

Tetrabutylammonium bromide, ACS reagent, ≥98.0%

216143

Sigma-Aldrich

Tetrabutylammonium fluoride solution, 1.0 M in THF

193119

Sigma-Aldrich

Tetrabutylammonium bromide, ReagentPlus^®, ≥99.0%