Halotrimethylsilane-nitrate salt reagent system has been shown to be an effective reagent for many organic synthetic transformations such as ipso-nitration of arylboronic acids, oxidation of sulfides and sulfoxides, and α-halogenation of acetophenones. We found that this system can be used as an efficient reagent for halogenation and ipso-nitration of cinnamic acids. Based on the ratio of the reagent components- halotrimethylsilane and the nitrate salt, the reaction can be tuned for halogenation or ipso-nitration. The reaction occurs under mild conditions and the products are obtained in excellent yields in most cases.

Halogenation and ipso-nitration of cinnamic acids: Halotrimethylsilane-nitrate, an efficient reagent system

253rd National Meeting (2017)

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