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- Title
Alkyne-Azide Cycloadditions with Copper Powder in a High-Pressure Continuous-Flow Reactor: High-Temperature Conditions versus the Role of Additives.
- Authors
Ötvös, Sándor B.; Mándity, István M.; Kiss, Lóránd; Fülöp, Ferenc
- Abstract
A safe and efficient flow-chemistry-based procedure is presented for 1,3-dipolar cycloaddition reactions between organic azides and acetylenes. This simple and inexpensive technique eliminates the need for costly special apparatus and utilizes Cu powder as a plausible CuI source. To maximize the reaction rates, high-pressure/high-temperature conditions are utilized; alternatively, the harsh reaction conditions can be moderated at room temperature by the joint application of basic and acidic additives. A comparison of the performance of these two approaches in a series of model reactions has resulted in the formation of useful 1,4-disubstituted 1,2,3-triazoles in excellent yields. The risks that are associated with the handling of azides are lowered, thanks to the benefits of flow processing, and gram-scale production has been safely implemented. The synthetic capability of this continuous-flow technique is demonstrated by the efficient syntheses of some highly functionalized derivatives of the antifungal .
- Publication
Chemistry - An Asian Journal, 2013, Vol 8, Issue 4, p800
- ISSN
1861-4728
- Publication type
Article
- DOI
10.1002/asia.201201125