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

被引：23

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

页码：8429 / 8434

页数：6

共 49 条

[1] Access to Divergent Fluorinated Enynes and Arenes via Palladium-Catalyzed Ring-Opening Alkynylation of gem-Difluorinated Cyclopropanes [J].