苯炔与二炔的[2＋2＋2]环加成反应制备菲类衍生物

Synthesis of Phenanthrene Derivatives through [2+2+2] Cycloaddition between Benzyne and Diynes

菲及菲类衍生物广泛应用于合成树脂、染料、农药和植物生长激素等领域。在无催化剂存在的条件下,利用苯炔的高反应活性,通过苯炔和偶联二炔获得了具有炔基功能基团的二取代的菲类化合物,产率为76%~83%。利用核磁共振和高分辨质谱等手段对所得化合物进行了结构解析：所得化合物是通过2个苯炔分子和1个二炔分子上的叁键间的[2＋2＋2]环加成反应实现的;二炔分子中残留的1个叁键可进一步功能化,制备其他菲类衍生物。

Phenanthrene and its derivatives are widely used in resins, dyes, agrochemicals and phytohormones, Several phenanthrene derivatives bearing alkynyl substituents were synthesized from benzyne and diynes with yields of 76%-83% in the absence of any catalyst. The structures of these compounds were characterized with 1H-NMR, ^13C-NMR and high resolution mass spectroscopy. The results showed that the phenanthrene derivatives were formed through the intermolecular [2＋2＋2] cycloaddition reaction of two benzyne molecules and one diyne molecule, leaving one triple bond which could be further functionalized to synthesize other phenanthrene derivatives.