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首页> 外文期刊>Chemistry: A European journal >Synthesis of Styrenes by Palladium(II)-Catalyzed Vinylation of Arylboronic Acids and Aryltrifluoroborates by Using Vinyl Acetate
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Synthesis of Styrenes by Palladium(II)-Catalyzed Vinylation of Arylboronic Acids and Aryltrifluoroborates by Using Vinyl Acetate

机译：钯（II）催化乙酸乙烯酯芳基硼酸和芳基三氟硼酸酯的乙烯基化合成苯乙烯

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摘要

Reactions of aromatic and heteroaromatic boronic acids or aryltrifluoroborate salts with vinyl acetate in the presence of a palladium(II) catalyst give the corresponding styrenes in good yields. This Heck reaction proceeds with microwave heating in less than 30 min at 140 degrees C in the absence of base and tolerates a variety of substituents. No palladium reoxidant is needed and the vinylation is performed under non-inert conditions. Mass spectrometry (electrospray ionization mass spectrometry (ESIMS) and tandem mass spectrometry (MS/MS)) was used to identify cationic palladium-containing complexes in ongoing reactions. The key intermediates that have been detected, together with experiments that used deuterated vinyl acetate, support the existence of catalytically active palladium hydride species, and that it is the arylation of ethylene, not vinyl acetate, which generates the styrene product. The mechanism of the reaction is discussed in terms of the palladium(II) intermediates mentioned above.
机译：在钯（II）催化剂存在下，芳族和杂芳族硼酸或芳基三氟硼酸盐与乙酸乙烯酯的反应以良好的收率得到相应的苯乙烯。在不存在碱的情况下，此Heck反应在140摄氏度下于不到30分钟的微波加热中进行，并能耐受各种取代基。不需要钯再氧化剂，并且乙烯基化在非惰性条件下进行。质谱法（电喷雾电离质谱法（ESIMS）和串联质谱法（MS / MS））用于鉴定正在进行的反应中的含阳离子钯的配合物。已检测到的关键中间体以及使用氘代乙酸乙烯酯的实验均支持存在催化活性的氢化钯物质，并且是乙烯（而不是乙酸乙烯酯）的芳基化生成了苯乙烯产品。根据上述钯（II）中间体讨论了反应机理。

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