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通过镍催化的串联烯烃双碳官能化和酸促进的环化-芳构化反应合成9-芳基甲基蒽衍生物的便捷途径

An Expedient Route to 9-arylmethylanthracene Derivatives via Tandem Ni-catalyzed Alkene Dicarbofunctionalization and Acid-promoted Cyclization-aromatization.

作者信息

Niroula Doleshwar, Sapkota Rishi R, Dhungana Roshan K, Shrestha Bijay, Giri Ramesh

机构信息

Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United States.

Department of Chemistry, University of Illinois, 600 South, Mathews Avenue, Urbana, Illinois 61801, United States.

出版信息

Isr J Chem. 2020 Mar;60(3-4):424-428. doi: 10.1002/ijch.201900158. Epub 2020 Feb 14.

Abstract

We report a nickel-catalyzed one pot synthesis of 9-arylmethylanthracene motifs, which find applications in medicinal and material chemistry. In this synthesis, we apply three component alkene dicarbofunctionalization of 2-vinylaldimines with aryl iodides and arylzinc reagent to generate a 1,1,2-diarylethyl scaffold, which then undergoes an acidpromoted cyclization followed by aromatization to furnish 9-arylmethylanthracene cores. With the new method, a number of differently-substituted 9-arylmethylanthracene derivatives can be synthesized in good yields.

摘要

我们报道了一种镍催化的一锅法合成9-芳基甲基蒽基序,该基序在药物化学和材料化学中具有应用价值。在该合成中,我们将2-乙烯基醛亚胺与芳基碘化物和芳基锌试剂进行三组分烯烃双碳官能化反应,生成1,1,2-二芳基乙基骨架,然后该骨架经过酸促进的环化反应,随后进行芳构化反应,得到9-芳基甲基蒽核。采用这种新方法,可以以良好的产率合成多种不同取代的9-芳基甲基蒽衍生物。

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