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Functionalized Alkynes

By: Matthias Junkers, Aldrich ChemFiles 2008, 8.1, 14.

Aldrich ChemFiles 2008, 8.1, 14.

Alkynes contain a highly versatile functional group that may be utilized for numerous reactions such as electrophilic additions of hydrogen, halogens, hydrogen halides, or water; metathesis; hydroboration; oxidative cleavage; C–C coupling; and cycloadditions. Terminal alkynes may be transformed into metal acetylides and can then be submitted to nucleophilic substitution with alkyl halides, forming new C–C bonds, or nucleophilic addition, e.g., the Favorskii reaction.

Sigma-Aldrich® furnishes a broad portfolio of alkynes consisting of more than 250 products. To see the full listing, please visit the organic building blocks section on Chem Product Central at: sigma-aldrich.com/chemprod.

From the class of cycloaddition reactions that can be performed with alkynes, the Huisgen 1,3-dipolar cycloaddition stands out and has found tremendous interest in recent years as the best representative of a “click” reaction. Alkyne building blocks with a second functionality are particularly useful in click chemistry. The second functional group allows the attachment of a molecule of interest that subsequently can be “clicked” conveniently to the target azide. The following product list contains alkynes with a free or protected hydroxyl functional group, halogen-bearing alkynes, and miscellaneous other alkynes with an additional functional group.

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