Gold(I)-Catalyzed Intermolecular Oxyarylation of Alkynes: Unexpected Regiochemistry in the Alkylatioin of Arenes
Gold(I)-Catalyzed Intermolecular Oxyarylation of Alkynes: Unexpected Regiochemistry in the Alkylatioin of Arenes
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DOI：
10.1021/ol9020578
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发表时间：
2009-11-05
期刊：
影响因子：
5.2
通讯作者：
Asensio, Gregorio
中科院分区：
文献类型：
--
作者：
Cuenca, Ana B.;Montserrat, Sergi;Asensio, Gregorio
乙炔和亚砜之间的反应，研究作为金催化的分子间加成的测试案例，提供了良好的产率的氧芳基化化合物3。不可预测的是，在所有情况下，获得由在邻近硫原子的位置处的亲电芳族烷基化产生的单一区域异构体，而不是预期的Friedel-Crafts区域异构体。提出了一种基于密度泛函理论计算的新的协同反应机理来解释金（I）分子间催化反应的产物。
The reaction between acetylenes and sulfoxides, studied as a test case for gold-catalyzed intermolecular addition, provides the oxyarylation compounds 3 in good yields. Unpredictably, in all cases a single regioisomer arising from the electrophilic aromatic alkylation at the position adjacent to the sulfur atom is obtained instead of the expected Friedel-Crafts regioisomer. A new concerted mechanism based on DFT calculations is proposed to account for the products in this intermolecular gold(I)-catalyzed reaction.