Hypervalent iodine-mediated gem-difluorination of vinyl halides enabled by exclusive 1,2-halo migration

被引：0

作者：

Chenglong Li ^{[1
]}

Yangzhen Liao ^{[1
]}

Xuemei Tan ^{[1
]}

Xiaozu Liu ^{[1
,2
]}

Peijun Liu ^{[1
,2
]}

WenXin Lv ^{[3
]}

Honggen Wang ^{[3
]}

机构：

[1] Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University

[2] Key Laboratory of Basic Pharmacology of Ministry of Education and Joint International Research Laboratory of Ethnomedicine of Ministry of Education, Zunyi Medical University

[3] Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen

来源：

Science China(Chemistry) | 2021年 / 06期

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D O I：

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摘要：

β-Difluorinated alkyl halides are of significant value in the modular synthesis of gem-difluorinated molecules. An exclusive 1,2-halo migratory gem-difluorination of vinyl halides with in situ-generated PhIF2·HF is described. This protocol provides a general and practical approach towards a wide variety of β-difluorinated alkyl bromides. Both α-and β-bromoalkyl alkenes are suitable substrates, leading to two distinct types of products. The extension of this protocol to vinyl chloride and iodide are also feasible.The synthetic versatility of this method has been highlighted by the late-stage modification of complex small molecules and further transformations of the β-difluorinated alkyl halides to valuable CF2-containing compounds.

引用

页数：5

共 10 条

[1] Hypervalent iodine-mediated gem-difluorination of vinyl halides enabled by exclusive 1,2-halo migration
Li, Chenglong
Liao, Yangzhen
Tan, Xuemei
Liu, Xiaozu
Liu, Peijun
Lv, Wen-Xin
Wang, Honggen
[J]. SCIENCE CHINA-CHEMISTRY, 2021, 64 (06) : 999 - 1003
[2] Hypervalent iodine-mediated gem-difluorination of vinyl halides enabled by exclusive 1,2-halo migration
Chenglong Li
Yangzhen Liao
Xuemei Tan
Xiaozu Liu
Peijun Liu
Wen-Xin Lv
Honggen Wang
[J]. Science China Chemistry, 2021, 64 (06) : 999 - 1003
[3] Hypervalent iodine-mediated gem-difluorination of vinyl halides enabled by exclusive 1,2-halo migration
Chenglong Li
Yangzhen Liao
Xuemei Tan
Xiaozu Liu
Peijun Liu
Wen-Xin Lv
Honggen Wang
[J]. Science China Chemistry, 2021, 64 : 999 - 1003
[4] Hypervalent iodine-mediated β-difluoroalkylboron synthesis via an unusual 1,2-hydrogen shift enabled by boron substitution
Lv, Wen-Xin
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[9] Chemoselective cycloisomerization of O-alkenylbenzamides via concomitant 1,2-aryl migration/elimination mediated by hypervalent iodine reagents
Jiaxin He
Feng-Huan Du
Chi Zhang
Yunfei Du
[J]. Communications Chemistry, 6
[10] Chemoselective cycloisomerization of O-alkenylbenzamides via concomitant 1,2-aryl migration/elimination mediated by hypervalent iodine reagents
He, Jiaxin
Du, Feng-Huan
Zhang, Chi
Du, Yunfei
[J]. COMMUNICATIONS CHEMISTRY, 2023, 6 (01)

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