Efficient and rapid synthesis of regioselective functionalized potassium 1,2,3-triazoletrifluoroborates via 1,3-dipolar cycloaddition |
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Authors: | Krishnavenu Bolla Taejung KimJung Ho Song Seokjoon LeeJungyeob Ham |
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Affiliation: | a MarineChemomics Laboratory, Natural Medicine Center, Korea Institute of Science and Technology, Gangneung 210-340, Republic of Korea b Department of Medicinal and Pharmaceutical Chemistry, University of Science and Technology, Daejeon 305-350, Republic of Korea c Department of Basic Science Kwandong, University College of Medicine, Gangneung 210-701, Republic of Korea |
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Abstract: | In this study, we present a previously unreported method of preparing regiospecific organo-[1,2,3]-triazol-1-aryl-trifluoroborates from haloaryltrifluoroborates via a one-pot 1,3-dipolar cycloaddition reaction. We found that the use of either electron-rich or electron-deficient haloaryltrifluoroborates led to the desired cycloaddition products with good to excellent yields. Furthermore, we successfully carried out the cross-coupling reactions of the obtained triazoles with various aryl halides by means of the Suzuki-Miyaura reaction in the presence of 3 mol % of Pd(PPh3)4 catalyst in a 20% aqueous 1,4-dioxane solution at 100 °C; all these reactions yielded complete conversion to the corresponding products. Besides providing a high level of personnel safety, our highly versatile approach allows the preparation of functionalized organotrifluoborates containing 1,2,3-triazoles with retained functionality. |
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Keywords: | Click chemistry 1,3-Dipolar addition Functionalized organotrifluoroborates Suzuki-Miyaura cross-coupling |
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