Revisiting Polyfluoroarenes as Radical Acceptors: Radical C-F Bond Borylation of Polyfluoroarenes with N-Heterocyclic Carbene Boranes and Synthesis of Borane-Containing Liquid Crystals

被引：16

作者：

Takahashi, Kosuke ^{[2
]}

Shimoi, Masaki ^{[2
]}

Watanabe, Takashi ^{[2
]}

Maeda, Katsuhiro ^{[2
]}

Geib, Steven J. ^{[1
]}

Curran, Dennis P. ^{[1
]}

Taniguchi, Tsuyoshi ^{[2
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

[2] Kanazawa Univ, Grad Sch Nat Sci & Technol, Kanazawa, Ishikawa 9201192, Japan

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 05期

基金：

美国国家科学基金会;

关键词：

AROMATIC FLUORO-DERIVATIVES; IPSO-SUBSTITUTION; HEXAFLUOROBENZENE; DEAROMATIZATION; ACTIVATION; ARYLATION; ACCESS; ARENES; RINGS;

D O I：

10.1021/acs.orglett.0c00481

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Polyfluoroarenes work as good radical acceptors in the thermal radical reaction with N-heterocyclic carbene boranes (NHC-boranes) in the presence of di-tert-butyl peroxide. In this reaction, a C-F bond of polyfluoroarenes is substituted with an NHC-boryl group to provide B-aryl NHC-borane derivatives. The developed synthetic method was applied to the synthesis of novel borane-containing liquid crystalline molecules having highly thermal stability.

引用

页码：2054 / 2059

页数：6

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