Copper-catalyzed oxidative dehydrogenative [3 + 2] annulation of oximes with α-amino ketones: entry to 3-aminopyrroles,Organic Chemistry Frontiers

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Copper-catalyzed oxidative dehydrogenative [3 + 2] annulation of oximes with α-amino ketones: entry to 3-aminopyrroles
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2024-08-23 , DOI: 10.1039/d4qo01307g
Yan-Yun Liu ₁ , Ming Hu ₂ , Jin-Heng Li _{2,

3,

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Affiliation

An unprecedented copper-catalyzed oxidative dehydrogenative [3 + 2] annulation of O-acyl oximes containing α-C(sp³)–H bonds with α-amino ketones for the preparation of 3-aminopyrroles is developed. This method uses O-acyl oximes as both internal oxidants and three-atom-unit components combined with the copper catalyst to drive catalytically generated oxime nitrogen-centered radicals and oxidative dehydrogenation of the α-amino ketones to form the key 2-iminoethan-1-one intermediates, enabling site-selective cleavage of the multiple α-C(sp³)–H bonds in O-acyl oximes and α-amino ketones to create two new bonds, including a C(sp²)–C(sp²) bond and a C(sp²)–N bond, between the carbon atoms and the nitrogen atom in a cross-selective fashion.

中文翻译：

铜催化肟与 α-氨基酮的氧化脱氢 [3 + 2] 环化：生成 3-氨基吡咯

开发了一种前所未有的铜催化氧化脱氢[3 + 2]环化含有α-C(sp ³ )–H键的O-酰基肟与α-氨基酮，用于制备3-氨基吡咯。该方法以O-酰基肟作为内氧化剂和三原子单元组分，与铜催化剂结合，驱动催化生成肟氮中心自由基，使α-氨基酮氧化脱氢形成关键的2-亚氨基乙烷-1 -one 中间体，能够对O-酰基肟和 α-氨基酮中的多个 α-C(sp ³ )–H 键进行位点选择性裂解，产生两个新键，包括 C(sp ² )–C(sp ² ) 键和 C(sp ² )–N 键，以交叉选择性方式位于碳原子和氮原子之间。

更新日期：2024-08-23

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