Strain-Promoted Azide–Alkyne Cycloadditions of Benzocyclononynes

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 azido...

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Bibliographic Details
Published in:Journal of organic chemistry 2012-03, Vol.77 (5), p.2093-2097
Main Authors: Tummatorn, Jumreang, Batsomboon, Paratchata, Clark, Ronald J, Alabugin, Igor V, Dudley, Gregory B
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Alkynes - chemistry
Azides - chemistry
Chemical reactivity
Chemistry
Cyclization
Cycloparaffins - chemistry
Exact sciences and technology
Kinetics and mechanisms
Models, Molecular
Molecular Structure
Organic chemistry
Preparations and properties
Reactivity and mechanisms
Stereoisomerism
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo300188y