Efficient Regioselective one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from in situ potassium arylethynyltrifluoroborates through Sonogashira Reaction
- Efficient Regioselective one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from in situ potassium arylethynyltrifluoroborates through Sonogashira Reaction
- 최필주; 송중호; 이명재; 김태정; 전상일; 함정엽
- triazole; sonogashira; potassium arylethynyltrifluoroborates
- Issue Date
- 2013 대한화학회 충북강원지부 광역 학술대회
- 1,4-Disubstituted 1,2,3-triazole derivatives, which are obtained from terminal alkynes and azides 1,3-dipolar cycloaddition, are important small-molecule building blocks for complex compounds, and hence find significant application in organic synthesis, pharmaceutical sciences, and development of functional materials. Terminal alkynes are expensive, have low molecular weights and boiling point, have a short shelf life(storage-instable), and are difficult to handle; these problems hinder the widespread use of terminal alkynes as 1,3-dipolar cycloaddition partners of azides.
Potassium arylethynyltrifluoroborates, the intermediates generated by the Sonogashira reaction of potassium ethynyltrifluroborate with various aryl halides, were directly coupled with azides in the presence of a stoichiometric amount of CuI under aqueous conditions, and desired 1,4-disubstituted 1,2,3-triazoles were isolated in good yields.
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