Fluoroalkylation-Borylation of Alkynes: An Efficient Method To Obtain (Z)-Tri- and Tetrasubstituted Fluoroalkylated Alkenylboronates

被引：67

作者：

Guo, Wen-Hao ^{[1
]}

Zhao, Hai-Yang ^{[1
]}

Luo, Zhi-Ji ^{[1
]}

Zhang, Shu ^{[2
]}

Zhang, Xingang ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, Key Lab Organofluorine Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China

[2] Univ Elect Sci & Technol China, Sch Mat & Energy, 2006 Xiyuan Ave,West High Tech Zone, Chengdu 611731, Sichuan, Peoples R China

来源：

ACS CATALYSIS | 2019年 / 9卷 / 01期

基金：

中国国家自然科学基金;

关键词：

alkynes; borylation; fluoroalkylated alkenylboronates; fluoroalkyl iodides; palladium; CROSS-COUPLING REACTION; PERFLUOROALKYL IODIDES; RADICAL-ADDITION; COPPER; ALKENES; BIS(PINACOLATO)DIBORON; FLUOROALKOXYLATION; TRIFLUOROSTYRENE; CARBOBORATION; FLUORINE;

D O I：

10.1021/acscatal.8b02842

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Efficient methods for the synthesis of fluoroalkylated alkenylboronates are very limited, despite their importance in modern organic synthesis. Herein, we report a palladium-catalyzed trans-fluoroalkylation-borylation of alkynes with fluoroalkyl iodides and B(2)pin(2). The reaction tolerates a series of difluoroalkyl iodides and perfluoroalkyl iodides and can enable coupling with a variety of alkynes, including internal and terminal alkynes, with high efficiency, high functional group compatibility, and high regio- and stereoselectivities. Preliminary mechanistic studies reveal that a trans-fluoroalkylated alkenyl iodide is the key intermediate, which subsequently undergoes borylation to produce the trans-fluoroalkylated alkenylboronate.

引用

页码：38 / 43

页数：11