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Minutes Synthesis of 1,4,5‐Trisubstituted 5‐Dialkylamino‐1,2,3‐triazoles by 1‐Copper(I)‐Alkyne Controlled Tandem Process
Author(s) -
Wang Bo,
Liu Nan,
Chen Wenwen,
Huang Dayun,
Wang Xinyan,
Hu Yuefei
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400471
Subject(s) - chemistry , electrophile , alkyne , copper , amine gas treating , combinatorial chemistry , triazole , tandem , oxidizing agent , medicinal chemistry , organic chemistry , catalysis , materials science , composite material
In existing CuAAC methods, the 1,4,5‐trisubstituted 1,2,3‐triazole unit usually was synthesized by trapping the 5‐metal‐1,2,3‐triazole intermediate (M=Cu, Bi or Al) with an electrophile. But, no 1,4,5‐trisubstituted 5‐dialkylamino‐1,2,3‐triazole has yet been synthesized for unknown reasons. We found that this problem may be caused by the strong oxidizing property of the amine electrophile (R 2 N + ) or by the low reactivity of the MC bond in the intermediate. However, when a polymeric complex 1‐copper(I)‐alkyne was used as a substrate, the highly reactive 5‐copper(I)‐1,2,3‐triazole intermediate formed smoothly in the presence of the amine electrophile (R 2 N + ). Finally, the first general synthesis of 1,4,5‐trisubstituted 5‐dialkylamino‐1,2,3‐triazoles was developed via the tandem reaction of 1‐copper(I)‐alkynes with azides and then with O ‐benzoyl hydroxylamines at room temperature which occurred within five minutes.