Palladium-Catalyzed Cross-Coupling of gem-Difluorocyclopropanes with gem-Diborylalkanes for the Synthesis of Boryl-Substituted Fluorinated Alkenes

被引：15

作者：

Ahmed, Ebrahim-Alkhalil M. A. ^{[2
]}

Zhang, Hongchen ^{[1
]}

Cao, Wen-Gen ^{[2
]}

Gong, Tian-Jun ^{[3
]}

机构：

[1] Wenzhou Med Univ, Coll Pharm, Wenzhou 325035, Peoples R China

[2] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China

[3] Univ Sci & Technol China, Hefei Natl Res Ctr Phys Sci Microscale, CAS Key Lab Urban Pollutant Convers, Anhui Prov Key Lab Biomass Clean Energy,iChEM, Hefei 230026, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 50期

基金：

中国国家自然科学基金;

关键词：

C-F BONDS; DIFLUORINATED CYCLOPROPANES; ENANTIOSELECTIVE SYNTHESIS; ALLYLIC SUBSTITUTION; ACCESS; ACTIVATION; PHARMACEUTICALS; FLUOROOLEFIN; ALKYLATION; ISOSTERES;

D O I：

10.1021/acs.orglett.3c03626

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This study presents a novel method for the regioselective coupling of gem-difluorinated cyclopropanes with gem-diborylmethane, utilizing a Pd-catalyst system. This innovative approach enables the synthesis of 2-fluoroalkenyl monoboronate scaffolds with high Z-selectivity. The resulting products undergo further transformations, including oxidation, Suzuki cross-coupling, and trifluoroborylation, all of which are achieved with good yields. This work introduces a valuable synthetic pathway to access important fluorinated compounds for various applications in organic chemistry.

引用

页码：9020 / 9024

页数：5

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