Rhodium acetate/base-catalyzed N-silylation of indole derivatives with hydrosilanes.

Rhodium acetate/base-catalyzed N-silylation of indole derivatives with hydrosilanes.

Chemical communications (Cambridge, England) (2012-08-10)

Shintaro Itagaki, Keigo Kamata, Kazuya Yamaguchi, Noritaka Mizuno

ABSTRACT

In the presence of Rh(2)(OAc)(4) (OAc = acetate) and TBA(2)WO(4) (TBA = tetra-n-butylammonium), the N-silylation of indole derivatives with hydrosilanes efficiently proceeded to give the corresponding N-silylated indoles in high yields. Pyrrole and carbazole were also N-silylated with the combined catalysts.

MATERIALS

Product Number

Brand

Product Description

86885

Sigma-Aldrich

Tetrabutylammonium perchlorate, ≥95.0% (T)

86893

Supelco

Tetrabutylammonium perchlorate, for electrochemical analysis, ≥99.0%

155837

Sigma-Aldrich

Tetrabutylammonium hydrogensulfate, 97%

230189

Sigma-Aldrich

Tetrabutylammonium hydroxide solution, 1.0 M in methanol

86854

Supelco

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

358665

Sigma-Aldrich

Tetrabutylammonium cyanide, 95%

86863

Sigma-Aldrich

Tetrabutylammonium hydroxide solution, 53.5-56.5% in H₂O

79989

Sigma-Aldrich

Tetrabutylammonium cyanide, technical, ≥80%

178780

Sigma-Aldrich

Tetrabutylammonium hydroxide solution, 40 wt. % in H₂O

268100

Sigma-Aldrich

Tetrabutylammonium phosphate monobasic solution, 1.0 M in H₂O

86880

Sigma-Aldrich

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

361399

Sigma-Aldrich

Tetrabutylammonium fluoride solution, 75 wt. % in H₂O

482285

Sigma-Aldrich

Rhodium(II) acetate dimer, 99.9% trace metals basis

216143

Sigma-Aldrich

Tetrabutylammonium fluoride solution, 1.0 M in THF

209058

Sigma-Aldrich

Rhodium(II) acetate dimer, powder

86852

Supelco

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

86868

Sigma-Aldrich

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

86857

Supelco

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

72453

Sigma-Aldrich

Tetrabutylammonium bisulfate solution, ~55% in H₂O

86890

Sigma-Aldrich

Tetrabutylammonium iodide, ≥99.0% (AT)

98479

Supelco

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

193119

Sigma-Aldrich

Tetrabutylammonium bromide, ReagentPlus^®, ≥99.0%

86833

Sigma-Aldrich

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

86870

Sigma-Aldrich

Tetrabutylammonium chloride, ≥97.0% (NT)

462144

Sigma-Aldrich

Tetrabutylammonium bromide solution, 50 wt. % in H₂O

140775

Sigma-Aldrich

Tetrabutylammonium iodide, reagent grade, 98%

86853

Supelco

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

86903

Supelco

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

651664

Sigma-Aldrich

Tetrabutylammonium azide

359173

Sigma-Aldrich

Tetrabutylammonium nitrate, 97%