Schnyder Anita, Indolese Adriano F
Solvias AG, Klybeckstrasse 191, CH-4002 Basel, Switzerland.
J Org Chem. 2002 Jan 25;67(2):594-7. doi: 10.1021/jo016076a.
Aroyl imides were prepared by a palladium-catalyzed aminocarbonylation reaction of aryl bromides with carbon monoxide and primary amides in good yields (58-72%). The reactions were carried out under mild conditions (5 bar, 120 degrees C) using 1 mol % of a palladium phosphine complex. Several aryl bromides were reacted with formamide, acetamide, benzamide, and benzenesulfonamide, respectively. For activated aryl bromides, a phosphine-to-palladium ratio of 2:1 was sufficient, but less reactive aryl bromides required a ligand-to-palladium ratio of 6:1 in order to stabilize the catalyst and achieve full conversion. The imides were very sensitive to aqueous basic conditions and were easily converted to aroyl amides or benzoic acids.
芳酰亚胺是通过芳基溴化物与一氧化碳及伯酰胺在钯催化的氨羰基化反应中以良好的产率（58 - 72%）制备得到的。反应在温和条件下（5巴，120℃）使用1摩尔%的钯膦配合物进行。几种芳基溴化物分别与甲酰胺、乙酰胺、苯甲酰胺和苯磺酰胺反应。对于活性较高的芳基溴化物，膦与钯的比例为2:1就足够了，但活性较低的芳基溴化物需要配体与钯的比例为6:1，以稳定催化剂并实现完全转化。这些亚胺对碱性水溶液条件非常敏感，很容易转化为芳酰胺或苯甲酸。
