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Tandem cyclization of α-cyano α-alkynyl aryl ketones induced by tert-butyl hydroperoxide and tetrabutylammonium iodide.

Organic letters (2012-11-30)
Ying-Chieh Wong, Chen-Tso Tseng, Tzu-Ting Kao, Yu-Cheng Yeh, Kak-Shan Shia
ABSTRACT

The radical cascade protocol of the α-cyano α-TMS/aryl-capped alkynyl aryl ketones promoted by tert-butyl hydroperoxide under catalysis with tetrabutylammonium iodide in refluxing benzene has been developed, leading to the construction of a variety of highly functionalized [6,6,5] tricyclic frameworks in an efficient manner.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Tetrabutylammonium hydroxide solution, 1.0 M in methanol
Sigma-Aldrich
Tetrabutylammonium hydroxide solution, 40 wt. % in H2O
Sigma-Aldrich
Tetrabutylammonium hydrogensulfate, 97%
Sigma-Aldrich
tert-Butyl hydroperoxide solution, 5.0-6.0 M in decane
Sigma-Aldrich
Tetrabutylammonium phosphate monobasic solution, 1.0 M in H2O
Sigma-Aldrich
Tetrabutylammonium cyanide, 95%
Sigma-Aldrich
tert-Butyl hydroperoxide solution, 5.0-6.0 M in nonane
Sigma-Aldrich
tert-Butyl hydroperoxide solution, 70 wt. % in H2O
Supelco
Tetrabutylammonium phosphate monobasic solution, suitable for ion pair chromatography, LiChropur, concentrate, ampule
Sigma-Aldrich
Tetrabutylammonium hydroxide solution, technical, ~40% in H2O (~1.5 M)
Sigma-Aldrich
Tetrabutylammonium perchlorate, ≥95.0% (T)
Supelco
Tetrabutylammonium hydroxide solution, ~40% in water, suitable for ion chromatography
Sigma-Aldrich
Tetrabutylammonium hydroxide solution, 54.0-56.0% in H2O
Supelco
Tetrabutylammonium perchlorate, for electrochemical analysis, ≥99.0%
Sigma-Aldrich
Tetrabutylammonium cyanide, technical, ≥80%
Sigma-Aldrich
Tetrabutylammonium bromide solution, 50 wt. % in H2O
Sigma-Aldrich
Tetrabutylammonium iodide, reagent grade, 98%
Sigma-Aldrich
Tetrabutylammonium fluoride solution, 1.0 M in THF
Sigma-Aldrich
Tetrabutylammonium bromide, ACS reagent, ≥98.0%
Sigma-Aldrich
Tetrabutylammonium fluoride solution, 75 wt. % in H2O
Sigma-Aldrich
Tetrabutylammonium nitrate, 97%
Supelco
Tetrabutylammonium iodide, suitable for ion pair chromatography, LiChropur, ≥99.0%
Supelco
Tetrabutylammonium bisulfate solution, suitable for ion pair chromatography, LiChropur, concentrate, ampule
Sigma-Aldrich
Tetrabutylammonium phosphate monobasic, puriss., ≥99.0% (T)
Sigma-Aldrich
Tetrabutylammonium iodide, ≥99.0% (AT)
Supelco
Tetrabutylammonium bromide, suitable for ion pair chromatography, LiChropur, ≥99.0%
Supelco
Tetrabutylammonium chloride, suitable for ion pair chromatography, LiChropur, ≥99.0%
Supelco
Tetrabutylammonium bisulfate, suitable for ion pair chromatography, LiChropur, ≥99.0%
Sigma-Aldrich
Tetrabutylammonium chloride, ≥97.0% (NT)