POLYFLUOROARENE-CAPPED THIOPHENE DERIVATIVES VIA FLUORIDE-CATALYZED NUCLEOPHILIC AROMATIC SUBSTITUTION

被引：2

作者：

Kikushima, Kotaro ^{[1
]}

Matsuki, Kana ^{[2
]}

Yoneda, Yuna ^{[2
]}

Menjo, Takayuki ^{[2
]}

Kaneko, Kosuke ^{[2
]}

Hanasaki, Tomonori ^{[2
]}

Dohi, Toshifumi ^{[1
]}

机构：

[1] Ritsumeikan Univ, Coll Pharmaceut Sci, Kusatsu 5258577, Japan

[2] Ritsumeikan Univ, Coll Life Sci, Dept Appl Chem, Kusatsu 5258577, Japan

来源：

HETEROCYCLES | 2021年 / 103卷 / 02期

关键词：

METAL-FREE SYNTHESIS; F BOND ACTIVATION; ELECTROCHEMICAL POLYMERIZATION; CONDUCTING POLYMERS; EFFICIENT SYNTHESIS; HYPERVALENT IODINE; ARYLATION; POLY(3,4-ETHYLENEDIOXYTHIOPHENE); ALKENYLATION;

D O I：

10.3987/COM-20-S(K)54

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Arylthiophene derivatives are potential components of functional materials, including organic electronics. Herein, we describe a nucleophilic aromatic substitution reaction of polyfluoroarenes using silylthiophenes as nucleophiles in the presence of a catalytic amount of a fluoride salt. Various polyfluoroarene-capped thiophene derivatives were synthesized via double arylation under transition metal-free conditions. A fluoride ion activates a silylthiophene to trigger a nucleophilic aromatic substitution, subsequently affording the coupling product along with elimination of the fluoride ion, which serves as a promoter of the catalytic reaction.

引用

页码：878 / 892

页数：15

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