Regioselective one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from in situ generated potassium arylethynyltrifluoroborates

Title
Regioselective one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from in situ generated potassium arylethynyltrifluoroborates
Authors
최필주송중호이명재김태정함정엽
Keywords
potassium arylethynyltrifluoroborates; 1,2,3-triazoles; regioselective one-pot synthesis
Issue Date
2013-10
Publisher
2013 추계 대한화학회
Abstract
1,4-Disubstituted 1,2,3-triazole derivatives, which are obtained from terminal alkynes and azides via 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 the desired 1,4-disubstituted 1,2,3-triazoles were isolated in good yields. Both electron-donating and electron-withdrawing substituents on the potassium arylethynyltrifluoroborates gave moderate-to-excellent isolated yields.
URI
http://pubs.kist.re.kr/handle/201004/46084
Appears in Collections:
KIST Publication > Conference Paper
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