Synthesis of carbocyclic aromatic compounds using ruthenium-catalyzed ring-closing enyne metathesis.
Synthesis of carbocyclic aromatic compounds using ruthenium-catalyzed ring-closing enyne metathesis.
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DOI：
10.1021/jo900456g
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发表时间：
2009-04
期刊：
影响因子：
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通讯作者：
Hidetoshi Takahashi;Kazuhiro Yoshida;A. Yanagisawa
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文献类型：
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作者：
Hidetoshi Takahashi;Kazuhiro Yoshida;A. Yanagisawa
报道了取代碳环芳香族化合物的一般合成方法。 1,5-辛二烯-7-yn-4-醇 6 的闭环烯炔复分解 (RCEM)/脱水和 1,5-辛二烯-7-yn-4-酮 7 的 RCEM/互变异构化分别提供了多种取代苯乙烯 4 和 4-乙烯基苯酚 8。通过利用 Sonogashira 偶联、烯丙基化和 Dess-Martin 氧化的组合，可以很容易地从 β-卤代-α,β-不饱和醛 9 或 3-卤代-2-丙烯-1-醇 13 制备无环前体 6 和 7。还介绍了用于合成1,3,5-三(1-苯基乙烯基)苯衍生物4r的RCEM/脱水和用于合成1,1'-联萘衍生物19a的RCEM/RCM/脱水作为该方法的应用。
General synthetic methods of substituted carbocyclic aromatic compounds are reported. Ring-closing enyne metathesis (RCEM)/dehydration of 1,5-octadien-7-yn-4-ols 6 and RCEM/tautomerization of 1,5-octadien-7-yn-4-ones 7 furnished a wide variety of substituted styrenes 4 and 4-vinylphenols 8, respectively. Acyclic precursors 6 and 7 were readily prepared from beta-halo-alpha,beta-unsaturated aldehydes 9 or 3-halo-2-propene-1-ols 13 by utilizing combinations of the Sonogashira coupling, allylation, and the Dess-Martin oxidation. The RCEM/dehydration for the synthesis of 1,3,5-tris(1-phenylethenyl)benzene derivative 4r and the RCEM/RCM/dehydration for the synthesis of 1,1'-binaphthyl derivative 19a are also presented as applications of this method.