Hydroamination versus Allylic Amination in Iridium-Catalyzed Reactions of Allylic Acetates with Amines: 1,3-Aminoalcohols via Ester-Directed Regioselectivity,Journal of the American Chemical Society

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Hydroamination versus Allylic Amination in Iridium-Catalyzed Reactions of Allylic Acetates with Amines: 1,3-Aminoalcohols via Ester-Directed Regioselectivity
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2018-07-10 , DOI: 10.1021/jacs.8b05683
Seung Wook Kim ₁ , Thomas Wurm ₁ , Gilmar A. Brito ₁ , Woo-Ok Jung ₁ , Jason R. Zbieg ₂ , Craig E. Stivala ₂ , Michael J. Krische ₁

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In the presence of a neutral dppf-modified iridium catalyst and Cs2CO3, linear allylic acetates react with primary amines to form products of hydroamination with complete 1,3-regioselectivity. The collective data, including deuterium labeling studies, corroborate a catalytic mechanism involving rapid, reversible acetate-directed aminoiridation with inner-sphere/outer-sphere crossover followed by turnover-limiting proto-demetalation mediated by amine.

中文翻译：

烯丙基乙酸酯与胺的铱催化反应中的氢化胺化与烯丙基胺化：1,3-氨基醇通过酯定向区域选择性

在中性 dppf 改性的铱催化剂和 Cs2CO3 存在下，线性烯丙基乙酸酯与伯胺反应形成具有完全 1,3-区域选择性的加氢胺化产物。包括氘标记研究在内的集体数据证实了一种催化机制，该机制涉及快速、可逆的醋酸盐导向氨基环化，内球/外球交叉，然后是由胺介导的限制营业额的原脱金属。

更新日期：2018-07-10

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