仲烷基卤化物在用于合成芳香杂环的多米诺芳基烷基化反应中的应用。
Application of secondary alkyl halides to a domino aryl alkylation reaction for the synthesis of aromatic heterocycles.
作者信息
Rudolph Alena, Rackelmann Nils, Turcotte-Savard Marc-Olivier, Lautens Mark
机构信息
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
出版信息
J Org Chem. 2009 Jan 2;74(1):289-97. doi: 10.1021/jo802180h.
A palladium-catalyzed, norbornene-mediated ortho-alkylation reaction of aryl iodides with secondary alkyl halides is described. Intermolecular or intramolecular ortho-alkylation proceeds in a domino process with various termination steps, generating two new carbon-carbon or carbon-nitrogen bonds in one pot, to afford an array of polycyclic heterocycles. The use of enantioenriched substrates has shown that this palladium-catalyzed reaction is stereospecific, proceeding with minimal erosion of ee.
本文描述了一种钯催化的、降冰片烯介导的芳基碘化物与仲烷基卤化物的邻位烷基化反应。分子间或分子内的邻位烷基化以多米诺过程进行，具有多种终止步骤，能在一锅反应中生成两个新的碳-碳键或碳-氮键，从而得到一系列多环杂环化合物。使用对映体富集的底物表明，这种钯催化反应具有立体专一性，在手性纯度（ee）上的损失极小。
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