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Synthesis of 2,2,6,6-Tetramethylpiperidin-1-yl-2-(2-cyanophenyl)-acetate by Transition Metal-Free Radical Cleavage Reaction from α-Bromoindanone
Received date: 2022-08-05
Revised date: 2022-10-31
Online published: 2022-12-28
Supported by
Ningxia Natural Science Foundation(2021AAC03100)
In this paper, the synthesis of 2,2,6,6-tetramethylpiperidin-1-yl-2-(2-cyanophenyl)acetate from bromoindanone with sodium azide and 2,2,6,6-tetramethylpiperidine nitrogen oxide was reported. The carbon-carbon bond cleavage of bromoindenone was realized with transition metal-free catalysis and a series of aryl 2-cyano-phenylacetate compounds were obtained. This method was an expansion of cyanophenylacetate’ synthesis, and the reaction mechanism was verified by computational chemistry. The experiment was carried out under mild conditions with transition metal-free catalysis and with broad substrate scope.
Jiao Qin , Jie Chen , Yan Su . Synthesis of 2,2,6,6-Tetramethylpiperidin-1-yl-2-(2-cyanophenyl)-acetate by Transition Metal-Free Radical Cleavage Reaction from α-Bromoindanone[J]. Chinese Journal of Organic Chemistry, 2023 , 43(6) : 2171 -2177 . DOI: 10.6023/cjoc202208006
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