Atom-Efficient Synthesis of Alkynylfluoroborates Using BF3-Based Frustrated Lewis Pairs

被引：31
|
作者：
Iashin, Vladimir [1 ]
Chernichenko, Konstantin [1 ]
Papai, Imre [2 ]
Repo, Timo [1 ]
机构：
[1] Univ Helsinki, Dept Chem, AI Virtasen Aukio 1, FI-00014 Helsinki, Finland
[2] Hungarian Acad Sci, Res Ctr Nat Sci, Magyar Tudosok Korutja 2, H-1117 Budapest, Hungary
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 45期
基金：
芬兰科学院;
关键词：
alkynes; amines; boron trifluoride; C-H activation; frustrated Lewis pairs; ORGANIC-SYNTHESIS; H-2; ACTIVATION; BORYLATION; REACTIVITY; BORON; BF3-CENTER-DOT-OET2; PERSPECTIVES; HETEROARENES; METALATIONS; MAGNESIUM;
D O I：
10.1002/anie.201608520
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A sterically demanding amine, 1,2,2,6,6-pentamethylpiperidine (PMP), forms a highly reactive Lewis acid-base pair with boron trifluoride. This pair reacts with terminal acetylenes to give the products of C(sp)-H borylation, previously unknown tri- and tetraalkynylboron compounds. Trialkynylfluoroborates can serve as surrogates of alkynyltrifluoroborates for C-C coupling reactions. Using aqueous NaOH, PMP can be recovered from its tetrafluoroborate salt, which is formed as a C-H borylation byproduct. Combining the discovered borylation reactivity with the PMP recovery provides a straightforward and atom-efficient approach to synthetically useful alkynylfluoroborates.
引用
收藏
页码：14146 / 14150
页数：5
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