Strain-Promoted Azide-Alkyne Cycloadditions of Benzocyclononynes

被引：44

作者：

Tummatorn, Jumreang ^{[1
]}

Batsomboon, Paratchata ^{[1
]}

Clark, Ronald J. ^{[1
]}

Alabugin, Igor V. ^{[1
]}

Dudley, Gregory B. ^{[1
]}

机构：

[1] Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 05期

基金：

美国国家科学基金会;

关键词：

CLICK CHEMISTRY; STABILIZATION;

D O I：

10.1021/jo300188y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Preliminary studies related to the design and development of new cycloalkyne reagents for metal-free click coupling are reported. Cydononynes are more stable than cyclooctynes, and the robust benzocyclononyne platform offers spontaneous reactivity toward azides at rates competitive with other azidophiles that have been employed for metal-free click coupling. Benzocyclononynes (e.g., 1) provide valuable insight into the design of new cycloalkynes for strain-promoted azide-alkyne cydoaddition (SPAAC) couplings for applications in which side reactions and decomposition of the reagent must be kept to a minimum.

引用

下载

页码：2093 / 2097

页数：5

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