Wu Xiuli, Zeng Yaxin, Jiang Zhong-Tao, Zhu Yulei, Xie Linshen, Xia Ying
West China School of Public Health and West China Fourth Hospital, West China-PUMC C.C. Chen Institute of Health and State Key Laboratory of Biotherapy, Sichuan University, Chengdu, Sichuan 610041, China.
Org Lett. 2022 Nov 18;24(45):8429-8434. doi: 10.1021/acs.orglett.2c03544. Epub 2022 Nov 4.
-Difluorinated cyclopropanes have attracted wide research interest in organic synthesis due to their high reactivity. Herein, we report a Lewis acid-catalyzed cross-coupling reaction of mono- and disubstituted -difluorinated cyclopropanes with nucleophiles. The formation of a fluoroallyl cation species triggered via the Lewis acid-assisted activation of the C-F bond is proposed in this transformation. The cation species is then trapped by the nucleophiles, including electron-rich arenes and allylsilanes, to deliver a series of fluoroallylic products in good yields. The reaction provides an alternative mode for using -difluorinated cyclopropanes as fluoroallyl surrogates.
二氟环丙烷因其高反应活性而在有机合成领域引起了广泛的研究兴趣。在此，我们报道了单取代和双取代二氟环丙烷与亲核试剂的路易斯酸催化交叉偶联反应。该转化过程中提出了通过路易斯酸辅助活化C-F键引发形成氟代烯丙基阳离子物种。然后该阳离子物种被亲核试剂捕获，包括富电子芳烃和烯丙基硅烷，以高收率得到一系列氟代烯丙基产物。该反应为使用二氟环丙烷作为氟代烯丙基替代物提供了一种替代模式。
