通过银催化氧化自由基脱羧反应便捷合成6-烷基菲啶和1-烷基异喹啉。
Convenient synthesis of 6-alkyl phenanthridines and 1-alkyl isoquinolines via silver-catalyzed oxidative radical decarboxylation.
作者信息
Yao Qian, Zhou Xin, Zhang Xiuli, Wang Cong, Wang Peng, Li Ming
机构信息
Key Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao, 266003, P.R. China.
出版信息
Org Biomol Chem. 2017 Jan 25;15(4):957-971. doi: 10.1039/c6ob02331b.
A convenient and efficient protocol for the synthesis of 6-alkyl phenanthridines and 1-alkyl isoquinolines has been developed. The reaction relies on the coupling of 2-isocyanobiphenyls and vinyl isonitriles with alkyl radicals formed by the silver-catalyzed decarboxylation of stoichiometric aliphatic carboxylic acids, and affords diverse phenanthridine and isoquinoline derivatives under mild reaction conditions. The experiment of β-scission of cyclobutylcarbinyl radicals is used to shed light on the reaction mechanism.
已开发出一种便捷高效的合成6-烷基菲啶和1-烷基异喹啉的方法。该反应依赖于2-异氰基联苯和乙烯基异腈与通过化学计量的脂肪族羧酸的银催化脱羧形成的烷基自由基的偶联，并在温和的反应条件下提供多种菲啶和异喹啉衍生物。利用环丁基甲基自由基的β-断裂实验来阐明反应机理。
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