Abstract
Primary aromatic amides are valuable compounds, which are generally prepared via Beckmann rearrangement of oximes and the hydration of nitriles in organic solvents. We investigated the environmentally friendly catalytic aminocarbonylation in water. Thus, a novel heterogeneous transition-metal catalyst, a polymer-supported terpyridine–palladium(II) complex, was prepared and found to promote azidocarbonylation of aryl iodides with NaN3 and to reduce the generated benzoyl azides in water under CO gas to yield primary aryl amides with high to excellent yield in a one-pot reaction. The catalyst was recovered and reused several times with no loss of catalytic activity.
Highlights
Primary amides are valuable compounds that are present in several natural products, are important structural motifs in pharmacologically active molecules [1], and are useful in engineering materials such as conductive polymers [2,3]
Upon screening screening the the reaction reaction conditions conditions for for the the aminocarbonylation aminocarbonylation in in water water with with the polymeric polymeric palladium found thatthat the reaction efficiency was greatly by simpleby reaction conditions
We examined the reduction of benzoyl azide (5)azide with polymeric polymeric catalyst because we postulate that one possible reaction intermediate isis polymeric
Summary
Primary amides are valuable compounds that are present in several natural products, are important structural motifs in pharmacologically active molecules [1], and are useful in engineering materials such as conductive polymers [2,3]. We developed the aminocarbonylation of aryl iodides to form primary amides in water using MeONH2 and a polymer-supported terpyridine–palladium(II) complex as an environmentally friendly synthesis; the reported reaction did not yield a high conversion efficiency [9]. Palladium-catalyzed carbonylation reactions of aromatic halides in the presence of several nucleophiles have undergone rapid development since the pioneering work of Heck and co-workers in 1974 [10]. In 2010, Beller and co-workers developed the palladium-catalyzed synthesis of primary amides using carbon monoxide and ammonia [12,13]. This reaction used gaseous ammonia and Pd(OAc)2 /dppf or Pd(OAc)2 /nBuP(1-Adamantyl) as the catalytic system. The toxicity of gaseous ammonia is the same as that of carbon monoxide at a threshold limit values of 50 ppm
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