金屬鈀催化雙異腈嵌入乙醯肟經由氧化性氮-氧鍵斷裂來合成2H-吡咯衍生物

Palladium-Catalyzed Double Isocyanide Insertion to Synthesize 2H-Pyrrole Derivatives via Oxidative N-O Cleavage of Acetyl Oximes

呂梃毅(Ting-Yi Lu)

指導教授 ： 王志鉦

高雄醫學大學/生命科學院/醫藥暨應用化學系碩士班/碩士(2016年)

摘要

乙醯肟與異腈經由鈀催化C-H官能化用於合成2-胺基吡咯-3-胺衍生物。反應是由乙醯肟透過金屬鈀進行氧化性氮-氧斷裂，生成亞烷基亞胺基鈀(II)再伴隨著兩當量異腈嵌入。此反應最大優點，具有廣泛的官能基團耐受性、良好的產率且乙醯肟可當作內部氧化劑。本反應可經由一鍋化(one-pot)之酸性水解來合成1H-吡咯-2,3-二酮類衍生物。

關鍵字

2H-吡咯 ； 金屬鈀 ； 異腈

並列摘要

A palladium-catalyzed CH functionalization of acetyl oxime with isocyanides has been developed for the synthesis of 2-iminopyrrol-3-amines. The reaction proceeds via oxidative NO cleavage of acetyl oxime to generate alkylideneimino-palladium (II) species followed by migratory double isocyanide insertion. The notable features of this reaction are broad functional group tolerance, good reaction yields, acetyl oxime as substrate and also as an internal oxidant. The scope of this reaction has been extended for the synthesis of 1H-pyrrole-2,3-dione in sequential one-pot via acid hydrolysis.

並列關鍵字

2H-Pyrrole ； Palladium ； Isocyanides

參考文獻

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