Efficient access to new chemical space through flow--construction of druglike macrocycles through copper-surface-catalyzed azide-alkyne cycloaddition reactions |
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Authors: | Bogdan Andrew R James Keith |
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Affiliation: | Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, California 92037, USA. |
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Abstract: | A series of 12‐ to 22‐membered macrocycles, with druglike functionality and properties, have been generated by using a simple and efficient copper‐catalyzed azide–acetylene cycloaddition reaction, conducted in flow in high‐temperature copper tubing, under environmentally friendly conditions. The triazole‐containing macrocycles have been generated in up to 90 % yield in a 5 min reaction, without resorting to the high‐dilution conditions typical of macrocyclization reactions. This approach represents a very efficient method for constructing this important class of molecules, in terms of yield, concentration, and environmental considerations. |
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Keywords: | click chemistry flow chemistry heterogeneous catalysis macrocycles synthetic methods |
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