ORGN 145 |
| Our lab has a long-standing interest in the design and synthesis of boronic acid-based fluorescent sensors for carbohydrates. Along this line, we have also developed a combinatorial approach to the synthesis of such sensors. For this we are in need of a large number of arylboronic acids with a terminal alkyne group, which can be used in the [2+3] Huisgen cycloaddition. Such ethynylaryl boronic acids (esters) were synthesized from commercially available bromoaryl boronic acids in three steps with good yields. The key reaction is microwave-facilitated selective formation of neopentyl trimethylsilylethynylaryl boronates by Sonogashira reaction from the corresponding bromides. The use of microwave was found to significantly improve the reaction yields and shorten the reaction time. |
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Asymmetric Reactions and Syntheses, Physical Organic Chemistry, Combinatorial Chemistry, Total Synthesis
8:00 PM-10:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Division of Organic Chemistry |