Chen Shuqi, Yao Yongqi, Yang Wen, Lin Qifu, Wang Lin, Li Huanyong, Chen Donghan, Tan Yun, Yang Dingqiao
Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment , South China Normal University , Guangzhou 510006 , People's Republic of China.
Analytical and Testing Center , Jinan University , Guangzhou 510632 , People's Republic of China.
J Org Chem. 2019 Sep 20;84(18):11863-11872. doi: 10.1021/acs.joc.9b01713. Epub 2019 Aug 30.
An efficient three-component cycloaddition of oxa(aza)bicyclic alkenes/norbornene in the presence of NaN and arylsulfonyl chlorides was developed, affording the corresponding aziridine products in good yields (up to 82%) with moderate to good / selectivities (up to >99:1 /). Further studies showed that the cycloaddition of oxa(aza)bicyclic alkenes in the presence of NaN and chloroalkanes could afford the -cycloadduct 1,2,3-triazolines in good to excellent yields (up to 95%). Compared with the existing methodologies, the current protocol demands very simple and mild reaction conditions and is a metal-free catalyzed reaction. In addition, a plausible mechanism for the cycloaddition reaction was also proposed.
开发了一种在NaN和芳基磺酰氯存在下，氧杂（氮杂）双环烯烃/降冰片烯的高效三组分环加成反应，以良好的产率（高达82%）和中等到良好的选择性（高达>99:1）得到相应的氮丙啶产物。进一步研究表明，在NaN和氯代烷烃存在下，氧杂（氮杂）双环烯烃的环加成反应能以良好到优异的产率（高达95%）得到环加成产物1, ,3-三唑啉。与现有方法相比，该方法所需的反应条件非常简单温和，且是无金属催化反应。此外，还提出了环加成反应的合理机理。
