One-pot synthesis of 5,5′-dibromo-2,2′-dipyridylacetylene and its boronic acid derivative |
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Authors: | Hyung Joon Jeon |
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Institution: | NanoCentury KAIST Institute, Graduate School of EEWS (WCU) and Department of Materials Science & Engineering, KAIST, Daejeon 305-701, Republic of Korea |
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Abstract: | 5,5′-Dibromo-2,2′-dipyridylacetylene was prepared from 2,5-dibromopyridine and (trimethylsilyl)acetylene via the new one-pot synthesis approach using a regioselective palladium-catalyzed coupling reaction with a 60% yield. Several protocols of lithium-halogen exchange were then attempted to synthesize 6,6′-(1,2-ethynediyl)bis3-pyridylboronic acid] from 5,5′-dibromo-2,2′-dipyridylacetylene. The former was successfully obtained with a 54% yield by a reverse addition method using toluene and THF and it showed potential as a useful building block for cross-coupling reactions in the formation of carbon-carbon bonds. |
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Keywords: | 2 5-Dibromopyridine 5 5&prime -Dibromo-2 2&prime -dipyridylacetylene 6 6&prime -(1 2-Ethynediyl)bis[3-pyridylboronic acid] |
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