Potassium (1-Organo-1H-1,2,3-triazol-4-yl)trifluoroborates from Ethynyltrifluoroborate via Regioselective One-Pot CuAAC Reaction
- Potassium (1-Organo-1H-1,2,3-triazol-4-yl)trifluoroborates from Ethynyltrifluoroborate via Regioselective One-Pot CuAAC Reaction
- 정규혁; 김태정; 송중호; 김용주; 함정엽
- Copper; Click chemistry; Boron; Nitrogen heterocycles; Cross-coupling
- Issue Date
- 2013 추계 대한화학회
- 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.
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