Potassium (1-Organo-1H-1,2,3-triazol-4-yl)trifluoroborates from Ethynyltrifluoroborate via Regioselective One-Pot CuAAC Reaction

Title
Potassium (1-Organo-1H-1,2,3-triazol-4-yl)trifluoroborates from Ethynyltrifluoroborate via Regioselective One-Pot CuAAC Reaction
Authors
정규혁김태정송중호김용주함정엽
Keywords
Copper; Click chemistry; Boron; Nitrogen heterocycles; Cross-coupling
Issue Date
2013-10
Publisher
2013 추계 대한화학회
Abstract
Being one of the most important structural motifs for the development of potentially bioactive molecules and new materials, 1,4-disubstituted 1,2,3- triazoles are widely used in various fields such as organic synthesis, medicinal chemistry, and materials science. However, despite significant recent improvements, the diversity of 1,2,3-triazoles that can be obtained through the CuAAC reaction is limited by the availability and high price of the terminal alkyne derivatives from commercial sources. Moreover, some low-molecular-weight alkynes are difficult to handle because of their low boiling points. Therefore, new facile and efficient methods to obtain multifariously C4-functionalized triazole compounds are still of synthetic interest. A novel series of 1,4-disubstituted 1,2,3-triazole-containing potassium trifluoroborates were prepared from the corresponding organohalides with potassium ethynyltrifluoroborate via regioselective one-pot Cu-catalyzed azide-alkyne cycloaddition (CuAAC) reaction in good to excellent yields. Further succeeded in Suzuki-Miyaura cross-coupling reaction of these organo 1,2,3-triazol-4-yltrifluoroborates with aryl and alkenyl bromides using of PdCl2(dppf)·CH2Cl2/TBAB system under microwave irradiation.
URI
http://pubs.kist.re.kr/handle/201004/46078
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KIST Publication > Conference Paper
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