Metal-free double azide addition to strained alkynes of an octadehydrodibenzo[12]annulene derivative with electron-withdrawing substituents

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Beilstein Journal of Organic Chemistry Pub Date : 2024-09-04 DOI:10.3762/bjoc.20.191

Naoki Takeda, Shuichi Akasaka, Susumu Kawauchi, Tsuyoshi Michinobu

引用次数: 0

Abstract

Strain-promoted azide–alkyne cycloaddition (SpAAC) is a powerful tool in the field of bioconjugation and materials research. We previously reported a regioselective double addition of organic azides to octadehydrodibenzo[12]annulene derivatives with electron-rich alkyloxy substituents. In order to increase the reaction rate, electron-withdrawing substituents were introduced into octadehydrodibenzo[12]annulene. In this report, the synthesis of new octadehydrodibenzo[12]annulene derivatives, regioselective double addition of organic azides, and an application to crosslinking polymers are described.

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Beilstein J. Org. Chem. 2024, 20, 2234–2241. doi:10.3762/bjoc.20.191

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八代氢二苯并[12]萘衍生物与具有电子撤回取代基的受约束炔的无金属双叠氮加成反应

摘要应变促进叠氮化物–炔环加成（SpAAC）是生物共轭和材料研究领域的一种有力工具。我们曾报道过有机叠氮化物与具有富电子烷氧基取代基的八代氢二苯并[12]蒽衍生物的区域选择性双加成反应。为了提高反应速率，我们在八代氢二苯并[12]萘中引入了抽电子取代基。本报告介绍了新的八代氢二苯并[12]萘衍生物的合成、有机叠氮化物的区域选择性双加成以及在交联聚合物中的应用。Chem.2024, 20, 2234–2241. doi:10.3762/bjoc.20.191

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来源期刊

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

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