Redox-Active Esters in Fe-Catalyzed C–C Coupling,Journal of the American Chemical Society

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Redox-Active Esters in Fe-Catalyzed C–C Coupling
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2016-08-29 , DOI: 10.1021/jacs.6b07172
Fumihiko Toriyama ₁ , Josep Cornella ₁ , Laurin Wimmer ₁ , Tie-Gen Chen ₁ , Darryl D. Dixon ₂ , Gardner Creech ₂ , Phil S. Baran ₁

Affiliation

Cross-couplings of alkyl halides and organometallic species based on single electron transfer using Ni and Fe catalyst systems have been studied extensively, and separately, for decades. Here we demonstrate the first couplings of redox-active esters (both isolated and derived in situ from carboxylic acids) with organozinc and organomagnesium species using an Fe-based catalyst system originally developed for alkyl halides. This work is placed in context by showing a direct comparison with a Ni catalyst for >40 examples spanning a range of primary, secondary, and tertiary substrates. This new C–C coupling is scalable and sustainable, and it exhibits a number of clear advantages in several cases over its Ni-based counterpart.

中文翻译：

Fe催化的C-C偶联中的氧化还原活性酯

几十年来，基于单电子转移使用 Ni 和 Fe 催化剂体系的烷基卤化物和有机金属物种的交叉偶联已被广泛且分别地研究。在这里，我们展示了氧化还原活性酯（从羧酸中分离和原位衍生）与有机锌和有机镁物种的首次偶联，使用最初为烷基卤化物开发的 Fe 基催化剂体系。这项工作通过展示与 Ni 催化剂的直接比较来放置在上下文中，涉及超过 40 个示例，涵盖一系列初级、二级和三级底物。这种新的 C-C 耦合具有可扩展性和可持续性，并且在某些情况下比其基于 Ni 的耦合表现出许多明显的优势。

更新日期：2016-08-29

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