Synthesis of tris(4-amino-2,6-dimethylphenyl)borane and facile extension of its ¦Ð-conjugated system by utilizing the reactivity of the amino groups

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• 作者：Junro Yoshino ; ^{yoshino@sci.u-toyama.ac.jp} ; Yuri Nakamura ; Shizuka Kunitomo ; Naoto Hayashi ; Hiroyuki Higuchi ; ^{higuchi@sci.u-toyama.ac.jp}
• 关键词：Triarylborane ; Extended ¦Ð-conjugated system ; Ullmann condensation ; Dehydration ; UV&ndash ; vis spectrum ; Theoretical calculation
• 刊名：Tetrahedron Letters
• 出版年：2013
• 出版时间：29 May, 2013
• 年：2013
• 卷：54
• 期：22
• 页码：2817-2820
• 全文大小：706 K

文摘

Tris(4-amino-2,6-dimethylphenyl)borane (1), a triarylborane bearing an unsubstituted amino group on all of its aryl substituents, and related triarylboranes were synthesized via Ullmann condensation. The facile dehydration reactions of 1 with benzaldehyde and nitrosobenzene gave tris[4-(benzylidenamino)-2,6-dimethylphenyl]borane and tris[2,6-dimethyl-4-(phenylazo)phenyl]borane, respectively. These triarylboranes bear an extended ¦Ð-conjugated system bridged by a nitrogen-containing ¦Ð-linker on each of their aryl groups. UV-vis absorption spectra and theoretical calculations revealed that the ¦Ð-conjugated system of the triarylborane was effectively extended by utilizing the reactivity of the amino groups.