M. Da̧browski, P. Kurach, Sergiusz Luliński
Apr 1, 2007
Citations
0
Influential Citations
27
Citations
Journal
Applied Organometallic Chemistry
Abstract
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 of various ortho-functionalized arylboronic acids. Specifically, reactions with benzaldehydes provide a convenient access to 1,3-dihydro-1-hydroxy-3-arylbenzo[c][2,1]oxaboroles that exhibit a remarkably high rotational barrier around the Caryl bond. In addition, the molecular structure of sterically hindered 1,3-dihydro-1-hydroxy-3-(2′, 6′-dimethoxyphenyl)benzo[c][2,1]oxaborole is reported. Copyright © 2007 John Wiley & Sons, Ltd.