A 1,3-Dihydro-1,3-azaborine Debuts,Journal of the American Chemical Society

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A 1,3-Dihydro-1,3-azaborine Debuts
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2011-12-21 , DOI: 10.1021/ja2097089
Senmiao Xu ₁ , Lev N Zakharov , Shih-Yuan Liu

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We present the first synthesis and characterization of a 1,3-dihydro-1,3-azaborine, a long-sought BN isostere of benzene. 1,3-Dihydro-1,3-azaborine is a stable structural motif with considerable aromatic character as evidenced by structural analysis and its reaction chemistry. Single crystal X-ray analysis indicates bonding consistent with significant electron delocalization. 1,3-Dihydro-1,3-azaborines also undergo nucleophilic substitutions at boron and electrophilic aromatic substitution reactions. In view of the versatility and impact of aromatic compounds in the biomedical field and in materials science, the present study further expands the available chemical space of arenes via BN/CC isosterism.

中文翻译：

A 1,3-Dihydro-1,3-azaborine 首次亮相

我们首次合成和表征了 1,3-dihydro-1,3-azaborine，这是一种长期寻找的苯的 BN 等排体。1,3-Dihydro-1,3-azaborine 是一种稳定的结构基序，具有相当大的芳香性，结构分析及其反应化学证明了这一点。单晶 X 射线分析表明键合与显着的电子离域一致。1,3-Dihydro-1,3-azaborines 也在硼和亲电芳香取代反应中发生亲核取代。鉴于芳香化合物在生物医学领域和材料科学中的多功能性和影响，本研究通过 BN/CC 等排结构进一步扩展了芳烃的可用化学空间。

更新日期：2011-12-21

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