Synthesis of Regioselective Functionalized Organotrifluoroborates via 1,3-Dipolar Cycloaddition Reaction
- Synthesis of Regioselective Functionalized Organotrifluoroborates via 1,3-Dipolar Cycloaddition Reaction
- 송중호; 김태정; 함정엽
- Organotrifluoroborate; 1,3-Dipolar Cycloaddition; Suzuki-Miyaura cross-coupling reaction; organoboron; 1, 2, 3-triazole; one-pot reaction; C-C bond formation; heterocycle
- Issue Date
- 2011년 대한화학회 강원/충북 추계 광역지부회
- Recently, organotrifluoroborate salts have been used as important synthetic reagents in the Suzuki-Miyaura cross-coupling reaction. Potassium organotrifluoroborates are easily prepared by the addition of inexpensive KHF2 to various organoboron intermediates, and they are stable to air and moisture. There has been no attempts for the preparation of organotrifluoroborate salt containing 1, 2, 3-triazoles. We are able to prepare 1, 2, 3-triazole ring system consisting of organoaryltrifluoroborates via a one-pot 1, 3-dipolar cycloaddition reaction between various terminal alkynes and haloaryltrifluoroborates with good yields under simple reaction conditions. Further, these substrates are shown for the C-C bond formation via Suzuki-Miyaura reaction which can play an important role in biologically important heterocycles such as antibacterial, antiallergic, anti-HIV activity, and antineoplastic activity. Besides providing a high level of personnel safety, our highly versatile approach allows the preparation of functionalized organotrifluoroborates containing 1,2,3-triazoles with retained functionality.
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