Anortho-lithiated derivative of protected phenylboronic acid: an approach toortho-functionalized arylboronic acids and 1,3-dihydro-1-hydroxybenzo[c][2,1]oxaboroles
作者： Marek D??browski , Paweł Kurach , Sergiusz Luliński , Janusz Serwatowski
DOI: 10.1002/AOC.1217
关键词:
摘要: 2-(2′-Bromophenyl)-6-butyl-[1,3,6,2]dioxazaborocan, prepared readily by the esterification of 2-bromophenylboronic acid with N-butyldiethanolamine (BDEA), undergoes Br/Li exchange using BuLi/THF at − 78 °C. A resulting intermediate proved useful in synthesis various ortho-functionalized arylboronic acids. Specifically, reactions benzaldehydes provide a convenient access to 1,3-dihydro-1-hydroxy-3-arylbenzo[c][2,1]oxaboroles that exhibit remarkably high rotational barrier around Caryl bond. In addition, molecular structure sterically hindered 1,3-dihydro-1-hydroxy-3-(2′, 6′-dimethoxyphenyl)benzo[c][2,1]oxaborole is reported. Copyright © 2007 John Wiley & Sons, Ltd.
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