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Efficient Access to New Chemical Space Through Flow—Construction of Druglike Macrocycles Through Copper‐Surface‐Catalyzed Azide–Alkyne Cycloaddition Reactions
Author(s) -
Bogdan Andrew R.,
James Keith
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201002215
Subject(s) - cycloaddition , acetylene , alkyne , copper , yield (engineering) , chemistry , azide , catalysis , combinatorial chemistry , photochemistry , organic chemistry , materials science , metallurgy
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.