Synthesis and characterization of boronates derived from non-symmetric amino-bis-phenols

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• 作者：Arturo Abreu ; S. Jesù ; s Alas ; Hiram I. Beltr&#xe1 ; n ; Rosa Santillan and Norberto Farf&#xe1 ; n
• 关键词：Boron ; Boronate ; Tridentate ligand ; X-ray crystallography ; NMR ; Supramolecular arrangement
• 刊名：Journal of Organometallic Chemistry
• 出版年：2006
• 期刊代码：64_0022328x
• 类别：ch
• 出版时间：15 January 2006
• 卷：691
• 期：3
• 页码：337-348
• 文件大小：396 K

摘要

The condensation of 2-[[(2-hydroxyphenyl)amino]methyl]-phenols (1a–1e) with different arylboronic acids led to 12 new monomeric boronates of the type 2-aryl-dibenzo[d,h]-6-aza-1,3-dioxa-2-boracyclononene (2a–2l). The boronates were characterized by ¹H-, ¹³C-, ¹¹B- and 2D-NMR experiments, FT infrared, mass spectra and elemental analyses. The stereochemistry of the H–N → B–Ph fusion is always cis, as established through the NMR spectra, as well as the X-ray structures of four boronates (2a, 2e, 2f and 2l). Hydrogen bonds between the amine proton and the oxygen ester of the five- membered ring are present in three X-ray structures (2a, 2e and 2f), while the supramolecular structure in the derivative possessing a primary amine (2l) is built up through the protons present in this moiety instead of the proton from the H–N → B–Ph fragment.