Lewis Acid-Catalyzed Ring-Opening Cross-Coupling Reaction of gem-Difluorinated Cyclopropanes Enabled by C-F Bond Activation

被引：20
作者：
Wu, Xiuli [1 ,2 ,3 ]
Zeng, Yaxin [1 ,2 ,3 ]
Jiang, Zhong-Tao [1 ,2 ,3 ]
Zhu, Yulei [1 ,2 ,3 ]
Xie, Linshen [1 ,2 ,3 ]
Xia, Ying [1 ,2 ,3 ]
机构：
[1] Sichuan Univ, West China Sch Publ Hlth, Chengdu 610041, Sichuan, Peoples R China
[2] Sichuan Univ, West China Hosp 4, State Key Lab Biotherapy, West China PUMC,C C Chen Inst Hlth, Chengdu 610041, Sichuan, Peoples R China
[3] Sichuan Univ, State Key Lab Biotherapy, Chengdu 610041, Sichuan, Peoples R China
来源：
ORGANIC LETTERS | 2022年 / 24卷 / 45期
关键词：
FUNCTIONALIZATION; ALKYLATION; ACCESS; ARENES;
D O I：
10.1021/acs.orglett.2c03544
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
gem-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 gem-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 gem-difluorinated cyclopropanes as fluoroallyl surrogates.
引用
收藏
页码：8429 / 8434
页数：6
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