Expanding the chemical space of enol silyl ethers: catalytic dicarbofunctionalization enabled by iron catalysis.
Expanding the chemical space of enol silyl ethers: catalytic dicarbofunctionalization enabled by iron catalysis.
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DOI：
10.1039/d3sc04549h
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发表时间：
2023-11-22
期刊：
影响因子：
8.4
通讯作者：
Gutierrez, Osvaldo
中科院分区：
文献类型：
--
作者：
Sar, Dinabandhu;Yin, Shuai;Grygus, Jacob;Renteria-Gomez, Angel;Garcia, Melanie;Gutierrez, Osvaldo
烯基硅基醚是在化学合成中广泛使用的通用性，可及可访问的底物，这些基序的常规反应性限于经典的两个电子（2-e）烯型烯型烯型烯型化学，而在一个cerveriation中，在一个电子（1-e）中，在两种情况下都可以用电动伴侣或作为自由基的反应性。操作简单的一步protocol that combines readily available fluoroalkyl halides, silyl enol ethers, and, for the first time, hetero(aryl) Grignard reagents to promote selective dicarbofunctionalization of enol silyl ethers. From a broader perspective, this work expands the synthetic utility of enol silyl ethers and establishes bisphosphine–iron catalysis as enabling technology capable of orchestrating selective C–C bond formations with short-lived α-sililyl radicals with practical对可持续化学合成的含义。
在本文中，我们通过Fe催化的（氟）烷基卤化物和烯醇尖龙硅烷基醚的Fe催化分解的交叉偶联来报告烯醇silyl Ethers的双核功能化。
Enol silyl ethers are versatile, robust, and readily accessible substrates widely used in chemical synthesis. However, the conventional reactivity of these motifs has been limited to classical two electron (2-e) enolate-type chemistry with electrophilic partners or as radical acceptors in one electron (1-e) reactivity leading, in both cases, to exclusive α-monofunctionalization of carbonyls. Herein we describe a mild, fast, and operationally simple one-step protocol that combines readily available fluoroalkyl halides, silyl enol ethers, and, for the first time, hetero(aryl) Grignard reagents to promote selective dicarbofunctionalization of enol silyl ethers. From a broader perspective, this work expands the synthetic utility of enol silyl ethers and establishes bisphosphine–iron catalysis as enabling technology capable of orchestrating selective C–C bond formations with short-lived α-silyloxy radicals with practical implications towards sustainable chemical synthesis. Herein, we report the dicarbofunctionalization of enol silyl ethers via an Fe-catalyzed decoupled cross-coupling of (fluoro)alkyl halides, and enol silyl ethers.
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