Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and Beyond,Journal of the American Chemical Society

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Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and Beyond
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-05-14 , DOI: 10.1021/jacs.0c03993
Kelvin Pak Shing Cheung ₁ , Daria Kurandina ₁ , Tetsuji Yata ₁ , Vladimir Gevorgyan ₁

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A photoinduced palladium-catalyzed 1,2-carbofunctionalization of conjugated dienes has been developed. This mild modular approach, which does not require employment of exogeneous photosensitizers and external oxidants, allows for efficient and highly regio- and ste-reoselective synthesis of a broad range of allylic amines from readily available 1,3-dienes, alkyl iodides, and amines. Employment of O- and C-nucleophiles toward oxyalkylation and dialkylation products was also demonstrated. A putative -allyl palladium radical-polar crossover path is proposed as a key event in this three-component coupling process. The utility of this protocol is highlighted by its appli-cation for derivatization of several amine-containing drugs.

中文翻译：

共轭二烯的光诱导钯催化碳官能化通过自由基-极性交叉场景进行：1,2-氨基烷基化及其他

已开发出光诱导钯催化的共轭二烯的 1,2-碳功能化。这种温和的模块化方法不需要使用外源光敏剂和外部氧化剂，允许从容易获得的 1,3-二烯、烷基碘和胺中高效且高度区域和立体选择性地合成各种烯丙胺. 还证明了使用 O-和 C-亲核试剂进行烷氧基化和二烷基化产物。推定的 π-烯丙基钯自由基 - 极性交叉路径被认为是该三组分耦合过程中的关键事件。该协议的实用性因其在几种含胺药物的衍生化中的应用而突出。

更新日期：2020-05-14

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