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Supported palladium catalyzed aminocarbonylation of aryl iodides employing bench-stable CO and NH3 surrogates.
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2020-08-28 , DOI: 10.1039/d0ob01445a
Shaifali 1 , Sheetal 1 , Rohit Bains 1 , Ajay Kumar 1 , Shankar Ram 1 , Pralay Das 1
Affiliation  

A simple, efficient and phosphine free protocol for carbonylative synthesis of primary aromatic amides under polystyrene supported palladium (Pd@PS) nanoparticle (NP) catalyzed conditions has been demonstrated. Herein, instead of using two toxic and difficult to handle gases simultaneously, we have employed the solid, economical, bench stable oxalic acid as the CO source and ammonium carbamate as the NH3 source in a single pot reaction. For the first time, we have applied two non-gaseous surrogates simultaneously under heterogeneous catalyst (Pd@PS) conditions for the synthesis of primary amides using an easy to handle double-vial (DV) system. The developed strategy showed a good functional group tolerance towards a wide range of aryl iodides and afforded primary aromatic amides in good yields. The Pd@PS catalyst was easy to separate and can be recycled up to four consecutive runs with small loss in catalytic activity. We have successfully extended the scope of the methodology to the synthesis of isoindole-1,3-diones from 1,2-dihalobenzene, 2-halobenzoates and 2-halobenzoic acid following double and single carbonylative cyclization approaches.

中文翻译:

使用工作台稳定的 CO 和 NH3 替代物支持钯催化的芳基碘的氨基羰基化。

已经证明了一种在聚苯乙烯负载的钯 (Pd@PS) 纳米颗粒 (NP) 催化条件下羰基化合成初级芳香酰胺的简单、高效且无膦的方案。在此,我们没有同时使用两种有毒且难以处理的气体,而是使用固体、经济、台式稳定的草酸作为 CO 源,使用氨基甲酸铵作为 NH 3源在一个单一的锅反应。我们首次在非均相催化剂 (Pd@PS) 条件下同时应用两种非气态替代物,使用易于处理的双样品瓶 (DV) 系统合成伯酰胺。所开发的策略显示出对广泛的芳基碘具有良好的官能团耐受性,并以良好的收率提供了初级芳香酰胺。Pd@PS 催化剂易于分离,最多可连续循环四次,催化活性损失很小。我们已经成功地将方法的范围扩展到通过双和单羰基化环化方法从 1,2-二卤代苯、2-卤代苯甲酸酯和 2-卤代苯甲酸合成异吲哚-1,3-二酮。
更新日期:2020-09-23
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