Anka-Lufford Lukiana L, Huihui Kierra M M, Gower Nicholas J, Ackerman Laura K G, Weix Daniel J
Department of Chemistry, University of Rochester, Rochester, NY, 14627-0216, USA.
Chemistry. 2016 Aug 8;22(33):11564-7. doi: 10.1002/chem.201602668. Epub 2016 Jul 8.
Cross-electrophile coupling of aryl halides with alkyl halides has thus far been primarily conducted with stoichiometric metallic reductants in amide solvents. This report demonstrates that the use of tetrakis(dimethylamino)ethylene (TDAE) as an organic reductant enables the use of non-amide solvents, such as acetonitrile or propylene oxide, for the coupling of benzyl chlorides and alkyl iodides with aryl halides. Furthermore, these conditions work for several electron-poor heterocycles that are easily reduced by manganese. Finally, we demonstrate that TDAE addition can be used as a control element to 'hold' a reaction without diminishing yield or catalyst activity.
迄今为止，芳基卤化物与烷基卤化物的交叉亲电偶联主要是在酰胺溶剂中使用化学计量的金属还原剂进行的。本报告表明，使用四（二甲基氨基）乙烯（TDAE）作为有机还原剂能够在非酰胺溶剂（如乙腈或环氧丙烷）中实现苄基氯和烷基碘与芳基卤化物的偶联。此外，这些条件适用于几种易被锰还原的缺电子杂环化合物。最后，我们证明添加TDAE可作为一种控制元素，用于“保持”反应，而不会降低产率或催化剂活性。
