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

页码：14146 / 14150

页数：5

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