Amine-directed Mizoroki–Heck arylation of free allylamines
Amine-directed Mizoroki–Heck arylation of free allylamines
复制标题
胺引导的游离烯丙胺的 Mizoroki–Heck 芳基化
DOI：
10.1039/d2qo00041e
复制
发表时间：
2022
影响因子：
5.4
通讯作者：
Young, Michael C.
中科院分区：
文献类型：
--
作者：
Landge, Vinod G.;Bonds, Audrey L.;Mncwango, Thandazile A.;Mather, Carolina B.;Saleh, Yasaman;Fields, Hunter L.;Lee, Frank;Young, Michael C.
过渡金属催化的Mizoroki-Heck反应是一种合成C-C键的有效方法，可以获得几种重要的药物。传统上，由于胺被过渡金属氧化或其他副反应，游离胺与这些方法不相容。然而，未受保护的烯丙胺的功能化特别有吸引力，因为它们在各种生物活性分子中普遍存在。本文报道了钯催化的游离烯丙胺选择性单芳基化反应。该策略适用于伯胺、仲胺和叔胺，使其非常普遍。我们的单芳基化方法是可扩展的，适用于具有各种取代芳烃或杂环基序的芳基碘化物，包括显色底物。
The transition metal-catalyzed Mizoroki–Heck reaction is a powerful method to synthesize C–C bonds, allowing access to several important pharmaceuticals. Traditionally free amines have not been compatible with these approaches due to oxidation of the amine by the transition metal or other side reactions. However, the functionalization of unprotected allylamines is particularly attractive due to their prevalence in various biologically active molecules. Herein we report the palladium-catalyzed selective monoarylation of free allylamines using aryl iodides. The strategy works on primary, secondary, and tertiary amines, making it very general. Our monoarylation method is scalable and works on aryl iodides with a variety of substituted arene or heterocycle motifs, including chromophoric substrates.