Palladium-Catalyzed Oxidative Amination of Unactivated Olefins with Primary Aliphatic Amines,Journal of the American Chemical Society

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Palladium-Catalyzed Oxidative Amination of Unactivated Olefins with Primary Aliphatic Amines
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2023-04-13 , DOI: 10.1021/jacs.3c02114
Mingda Li ₁ , Yangbin Jin ₁ , Yupeng Chen ₁ , Wanqing Wu ₁ , Huanfeng Jiang ₁

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Direct coupling of unactivated olefins with primary alkylamines is considered to be an efficient but unknown method for the construction of complex amines. Herein we report a catalytic intermolecular oxidative amination of unactivated olefins with primary aliphatic amines based on the combination of a palladium catalyst, a bidentate phosphine ligand, and duroquinone. A range of secondary allylic amines were obtained in good yields with excellent regio- and stereoselectivity. Mechanistic control experiments revealed that the reaction proceeds by allylic C(sp³)–H activation and nucleophilic amination. The utility of the protocol is further demonstrated with the late-stage modification and streamlined synthesis of drug molecules.

中文翻译：

钯催化的未活化烯烃与脂肪族伯胺的氧化胺化反应

未活化的烯烃与伯烷基胺的直接偶联被认为是构建复杂胺的有效但未知的方法。在此，我们报道了基于钯催化剂、双齿膦配体和二氢醌的组合，未活化烯烃与脂肪族伯胺的催化分子间氧化胺化。以良好的收率获得了一系列仲烯丙胺，具有出色的区域选择性和立体选择性。机械控制实验表明，反应通过烯丙基 C(sp ³ )–H 活化和亲核胺化进行。通过药物分子的后期修改和简化合成，进一步证明了该协议的实用性。

更新日期：2023-04-13

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