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

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 bromide, ACS reagent, ≥98.0%
Sigma-Aldrich
Tetrabutylammonium phosphate monobasic, puriss., 99% (T)
Sigma-Aldrich
Tetrabutylammonium bromide, ReagentPlus®, ≥99.0%
Sigma-Aldrich
Tetrabutylammonium iodide, reagent grade, 98%
Sigma-Aldrich
Tetrabutylammonium bisulfate, puriss., ≥99.0% (T)
Sigma-Aldrich
Tetrabutylammonium perchlorate, ≥95.0% (T)
Sigma-Aldrich
Tetrabutylammonium hydroxide solution, 1.0 M in methanol
Sigma-Aldrich
Tetrabutylammonium hydroxide solution, 40 wt. % in H2O
Sigma-Aldrich
Tetrabutylammonium hydrogensulfate, 97%
Supelco
Tetrabutylammonium hydroxide solution, ~40% in water, suitable for ion chromatography
Sigma-Aldrich
Tetrabutylammonium hydroxide solution, technical, ~40% in H2O (~1.5 M)