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Tetrabutylammonium iodide catalyzed synthesis of allylic ester with tert-butyl hydroperoxide as an oxidant.

Organic letters (2012-06-27)
Erbo Shi, Ying Shao, Shulin Chen, Huayou Hu, Zhaojun Liu, Jie Zhang, Xiaobing Wan
ABSTRACT

A metal-free C-H oxidation for the construction of allylic esters has been developed. The use of a commercially available and inexpensive catalyst and oxidant, and readily available starting materials, coupled with the operational simplicity of the reaction, renders the methodology a useful alternative to other approaches typically employed in the synthesis of allylic esters.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Tetrabutylammonium fluoride solution, 1.0 M in THF
Supelco
Tetrabutylammonium hydroxide solution, ~40% in water, suitable for ion chromatography
Sigma-Aldrich
Tetrabutylammonium hydroxide solution, 40 wt. % in H2O
Sigma-Aldrich
Tetrabutylammonium hydrogensulfate, 97%
Sigma-Aldrich
Tetrabutylammonium hydroxide solution, 1.0 M in methanol
Sigma-Aldrich
Tetrabutylammonium bromide, ACS reagent, ≥98.0%
Sigma-Aldrich
Tetrabutylammonium phosphate monobasic, puriss., ≥99.0% (T)
Sigma-Aldrich
Tetrabutylammonium chloride, ≥97.0% (NT)
Sigma-Aldrich
Tetrabutylammonium bisulfate, puriss., ≥99.0% (T)
Sigma-Aldrich
Tetrabutylammonium iodide, reagent grade, 98%
Sigma-Aldrich
Tetrabutylammonium phosphate monobasic solution, 1.0 M in H2O
Supelco
Tetrabutylammonium perchlorate, for electrochemical analysis, ≥99.0%
Supelco
Tetrabutylammonium bisulfate, suitable for ion pair chromatography, LiChropur, ≥99.0%
Sigma-Aldrich
Tetrabutylammonium perchlorate, ≥98.0% (T)
Sigma-Aldrich
Tetrabutylammonium hydroxide solution, technical, ~40% in H2O (~1.5 M)
Supelco
Tetrabutylammonium bromide, suitable for ion pair chromatography, LiChropur, ≥99.0%
Sigma-Aldrich
Tetrabutylammonium cyanide, 95%
Sigma-Aldrich
Tetrabutylammonium iodide, ≥99.0% (AT)
Sigma-Aldrich
Tetrabutylammonium azide
Sigma-Aldrich
Tetrabutylammonium hydroxide solution, 54.0-56.0% in H2O
Sigma-Aldrich
Tetrabutylammonium fluoride solution, 75 wt. % in H2O
Supelco
Tetrabutylammonium chloride, suitable for ion pair chromatography, LiChropur, ≥99.0%
Sigma-Aldrich
Tetrabutylammonium nitrate, 97%
Supelco
Tetrabutylammonium bisulfate solution, suitable for ion pair chromatography, LiChropur, concentrate, ampule
Sigma-Aldrich
Tetrabutylammonium bromide solution, 50 wt. % in H2O
Supelco
Tetrabutylammonium phosphate monobasic solution, suitable for ion pair chromatography, LiChropur, concentrate, ampule
Sigma-Aldrich
Tetrabutylammonium cyanide, technical, ≥80%
Sigma-Aldrich
Tetrabutylammonium bisulfate solution, ~55% in H2O
Supelco
Tetrabutylammonium iodide, suitable for ion pair chromatography, LiChropur, ≥99.0%