Palladium-Catalyzed H/D Exchange Reaction with 8-Aminoquinoline as the Directing Group: Access to ortho-Selective Deuterated Aromatic Acids and β-Selective Deuterated Aliphatic Acids,The Journal of Organic Chemistry

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Palladium-Catalyzed H/D Exchange Reaction with 8-Aminoquinoline as the Directing Group: Access to ortho-Selective Deuterated Aromatic Acids and β-Selective Deuterated Aliphatic Acids
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2018-07-04 00:00:00 , DOI: 10.1021/acs.joc.8b00734
Donghong Zhao ₁ , Haofan Luo ₁ , Binhui Chen ₁ , Wenteng Chen ₁ , Guolin Zhang ₁ , Yongping Yu ₁

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We develop a palladium-catalyzed H/D exchange reaction with 8-aminoquinoline as the directing group as well as D₂O as the source of deuterium atom and solvent. This reaction achieves selectively H/D exchange at the ortho-C–H of aromatic amides and the β-C–H of aliphatic amide. Ortho-deuterated aromatic acids and β-deuterated aliphatic acids are obtained by removal of the directing group. And a possible mechanism is also proposed.

中文翻译：

以8-氨基喹啉为指导基团的钯催化的H / D交换反应：获得邻位选择性氘代芳族酸和β选择性氘代脂族酸

我们开发了一种钯催化的H / D交换反应，该反应以8-氨基喹啉为导向基团，D ₂ O为氘原子和溶剂的来源。该反应在芳族酰胺的邻-C–H和脂族酰胺的β-C–H处选择性地实现H / D交换。通过除去该导向基团，可以得到邻氘代的芳族酸和β氘代的脂族酸。并提出了一种可能的机制。

更新日期：2018-07-04

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