对甲苯亚磺酸钠/KI介导端炔的需氧氧化碘代反应合成1-碘代炔和1,3-二炔
收稿日期: 2020-07-09
修回日期: 2020-09-11
网络出版日期: 2020-10-12
基金资助
国家自然科学基金(21602035); 广东省自然科学基金(2016A030307030); 广东石油化工学院创新研究团队(519124)
Sodiump-Toluenesulfinate/KI-Mediated Aerobic Oxidative Iodination of Terminal Alkynes for Synthesis of 1-Iodoalkynes and 1,3-Diynes
Received date: 2020-07-09
Revised date: 2020-09-11
Online published: 2020-10-12
Supported by
the National Natural Science Foundation of China(21602035); the Natural Science Foundation of Guangdong Province(2016A030307030); the Program for Innovative Research Team of Guangdong University of Petrochemical Technology(519124)
周鹏 , 冯尚伟 , 邱会华 , 张建涛 . 对甲苯亚磺酸钠/KI介导端炔的需氧氧化碘代反应合成1-碘代炔和1,3-二炔[J]. 有机化学, 2021 , 41(1) : 394 -399 . DOI: 10.6023/cjoc202007031
A practical and environmentally friendly protocol for the synthesis of 1-iodoalkynes was developed via sodium sulfinate-KI mediated aerobic oxidative iodination of terminal alkynes. This transformation features simple operation, high efficiency, broad functional-group tolerance and mild reaction conditions. Especially, dioxygen was used in these reactions which avoided the addition of hazardous or toxic oxidants. Moreover, for the purpose of increasing the synthetic utility of this method, an efficient transition-metal-free synthetic approach to symmetrical 1,3-diynes was developed via the iodination/ homocoupling of terminal alkynes in a one-pot manner.
Key words： terminal alkyne; 1-iodoalkyne; air; sodium sulfinate; 1,3-diyne
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