有机卤化物与烯丙基醋酸盐的选择性交叉偶联。
Selective cross-coupling of organic halides with allylic acetates.
机构信息
Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, USA.
出版信息
J Org Chem. 2012 Nov 16;77(22):9989-10000. doi: 10.1021/jo302086g. Epub 2012 Nov 6.
Abstract
A general protocol for the coupling of haloarenes with a variety of allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieved by the use of a very hindered ligand and more reactive, branched allylic acetates.
摘要
本文提出了一种将各种烯丙基乙酸酯与卤代芳烃偶联的通用方法。该方法的优点包括对亲电（酮、醛）和酸性（磺酰胺、三氟乙酰胺）底物的耐受性，以及与各种取代烯丙基乙酸酯偶联的能力。在稍作修改的条件下，仲烷基溴化物也可以进行烯丙基化，这证明了该方法的通用性。最后，通过使用位阻较大的配体和更活泼的支链烯丙基乙酸酯，可以实现活性乙烯基卤化物的偶联。
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