Green Synthesis and Catalysis Pub Date : 2023-06-08 , DOI: 10.1016/j.gresc.2023.06.001 Nagaraju Sakkani , Dhiraj K. Jha , Nouraan Sadiq , Parisa Sharif , John C.G. Zhao
An organocatalytic Markovnikov-type bromo-aminoxidation of styrene derivatives was achieved by using in-situ-generated bromine and N-oxyl radicals, and the desired products were obtained in moderate to good yields. The bromine radical was generated from phenyliodine(III) bis(3-bromopropionate) through consecutive decarboxylation and deethylenation reactions via an organocatalytic SET process. Phenyliodine(III) bis(3-bromopropionate) also served as the oxidant for the generation of the N-oxyl radicals, while the N-oxyl radical was also crucial for the generation of the key β-enaminyl radical intermediate that was required for the SET process.
中文翻译:
用于有机催化的乙烯基芳烃的马尔可夫尼科夫型溴氨基氧化反应中合成苯基碘(III)双(3-溴丙酸酯)
利用原位产生的溴和N-氧基自由基实现了苯乙烯衍生物的有机催化马尔可夫尼科夫型溴氨基氧化反应,并以中等至良好的收率获得了所需的产物。溴自由基是由双(3-溴丙酸)苯碘(III)通过有机催化 SET 过程连续脱羧和脱乙烯反应产生的。苯碘(III)双(3-溴丙酸酯)还充当产生N-氧基自由基的氧化剂,而N-氧基自由基对于生成关键的β-烯氨基自由基中间体也至关重要。设置过程。