Strain-promoted azide-alkyne cycloadditions of benzocyclononynes.
Strain-promoted azide-alkyne cycloadditions of benzocyclononynes.
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应变促进的苯并环壬炔的叠氮-炔环加成。
DOI：
10.1021/jo300188y
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发表时间：
2012
期刊：
影响因子：
--
通讯作者：
G. Dudley
中科院分区：
文献类型：
--
作者：
J. Tummatorn;Paratchata Batsomboon;R. Clark;I. Alabugin;G. Dudley
本文报道了用于无金属咔嗒偶联的新型环炔试剂的设计和开发的初步研究。旋环炔比环环炔更稳定，并且强大的苯并环环炔平台提供了对叠氮化物的自发反应性，其速度与用于无金属咔嗒偶联的其他亲氮试剂相比具有竞争力。苯并环壬炔（例如，1）为设计用于菌株促进叠氮-炔环加成（SPAAC）偶联的新型环炔提供了有价值的见解，用于必须将试剂的副反应和分解保持在最低限度的应用。
Preliminary studies related to the design and development of new cycloalkyne reagents for metal-free click coupling are reported. Cyclononynes 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 cycloaddition (SPAAC) couplings for applications in which side reactions and decomposition of the reagent must be kept to a minimum.