银催化脂肪族羧酸的脱羧叠氮化反应
Silver-Catalyzed Decarboxylative Azidation of Aliphatic Carboxylic Acids.
作者信息
Zhu Yuchao, Li Xinyao, Wang Xiaoyang, Huang Xiaoqiang, Shen Tao, Zhang Yiqun, Sun Xiang, Zou Miancheng, Song Song, Jiao Ning
机构信息
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , Xue Yuan Road 38, Beijing 100191, China.
State Key Laboratory of Elemento-organic Chemistry, Nankai University , Weijin Road 94, Tianjin 300071, China.
出版信息
Org Lett. 2015 Oct 2;17(19):4702-5. doi: 10.1021/acs.orglett.5b02155.
The catalytic decarboxylative nitrogenation of aliphatic carboxylic acids for the synthesis of alkyl azides is reported. A series of tertiary, secondary, and primary organoazides were prepared from easily available aliphatic carboxylic acids by using K2S2O8 as the oxidant and PhSO2N3 as the nitrogen source. The EPR experiment sufficiently proved that an alkyl radical process was generated in the process, and DFT calculations further supported the SET process followed by a stepwise SH2 reaction to afford azide product.
报道了用于合成烷基叠氮化物的脂肪族羧酸的催化脱羧氮化反应。通过使用过硫酸钾（K2S2O8）作为氧化剂和苯磺酰叠氮（PhSO2N3）作为氮源，从容易获得的脂肪族羧酸制备了一系列叔、仲和伯有机叠氮化物。电子顺磁共振（EPR）实验充分证明该过程中产生了烷基自由基过程，密度泛函理论（DFT）计算进一步支持了单电子转移（SET）过程，随后是逐步的SN2反应以得到叠氮化物产物。
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