2010
DOI: 10.1039/c003692g
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Direct amination of aryl halides with ammonia

Abstract: The traditional homogeneous access to aromatic amine derivatives is a nucleophilic aromatic substitution of the corresponding aryl halides. The halogen atom is usually relatively inert to amination reaction unless it is activated by the presence of electron withdrawing groups. Consequently, there has been particular emphasis over the past decade on the synthesis of metal complexes that are active catalysts for the preparation of aromatic amines. This tutorial review focuses on the use of metal-based complexes … Show more

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Cited by 204 publications
(83 citation statements)
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“…Ammonia (NH 3 ), a low cost but efficient refrigerant is highly important gas for its application in agriculture, cold storage, fertilizer, anti-fungal agent and other chemical industries123. The worldwide production of ammonia is about 100 million tons.…”
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confidence: 99%
“…Ammonia (NH 3 ), a low cost but efficient refrigerant is highly important gas for its application in agriculture, cold storage, fertilizer, anti-fungal agent and other chemical industries123. The worldwide production of ammonia is about 100 million tons.…”
mentioning
confidence: 99%
“…Therefore, a variety of protocols for synthesizing functionalized anilines have been developed [7][8][9][10][11][12][13][14][15][16][17][18][19]. The desirable method for the synthesis of functionalized anilines is the reduction of nitroarenes using transition metal catalysts in the presence of sodium tetrahydroborate (NaBH 4 ) [20].…”
Section: Introductionmentioning
confidence: 99%
“…In toluene, 31 % of benzamide was obtained ( Table 2, entry 1), while a yield of 52 % was achieved in DME (Table 2, entry 3). To our delight DMSO, CH 3 CN, and NMP gave improved yields up to 69 % ( Table 2, entries [4][5][6]. Considering the properties of solvents, CH 3 CN was chosen for our further studies as the reaction solvent.…”
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confidence: 99%
“…[3] In recent years, also palladium-catalyzed carbonylation reactions of aryl halides have been used for the production of primary amides (Scheme 1, pathway b). [4] However, only few of these protocols use economically and ecologically favorable ammonia as reagent [5] for the synthesis of primary amides. In general, more sophisticated ammonia synthons are employed as nucleophilic partner in the carbonylation reaction.…”
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confidence: 99%