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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.
    Author: Ötvös SB, Mándity IM, Kiss L, Fülöp F.
    Journal: Chem Asian J; 2013 Apr; 8(4):800-8. PubMed ID: 23404792.
    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 Cu(I) 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 cispentacin.
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