Fragment Couplings via CO2 Extrusion-Recombination: Expansion of a Classic Bond-Forming Strategy via Metallaphotoredox.
Fragment Couplings via CO2 Extrusion-Recombination: Expansion of a Classic Bond-Forming Strategy via Metallaphotoredox.
复制标题
DOI：
10.1021/jacs.5b08304
复制
发表时间：
2015-09-23
影响因子：
15
通讯作者：
MacMillan DW
中科院分区：
文献类型：
--
作者：
Le CC;MacMillan DW
在这项研究中，我们证明了分子片段可以很容易地通过简单的原位RO-C=OR成键反应偶联，随后在金属光氧化还原催化下，可以进行金属插入-脱羧基-复合生成Csp2-Csp3键。在该实施例中，以良好到高的产率完成了多种混合酸酐(由羧酸和酰氯原位形成)到片段偶联酮的转化。还描述了使用这种新的脱羧基重组方案合成药物埃迪伏西汀的三步法。
In this study we demonstrate that molecular fragments, which can be readily coupled via a simple, in situ RO—C=OR bond-forming reaction, can subsequently undergo metal insertion–decarboxylation–recombination to generate Csp2–Csp3 bonds when subjected to metallaphotoredox catalysis. In this embodiment the conversion of a wide variety of mixed anhydrides (formed in situ from carboxylic acids and acyl chlorides) to fragment-coupled ketones is accomplished in good to high yield. A three-step synthesis of the medicinal agent edivoxetine is also described using this new decarboxylation–recombination protocol.