Photochemical and Additive-free Coupling Reaction of α-Cumyl α-Ketoesters via Intermolecular C-H Bond Activation
Photochemical and Additive-free Coupling Reaction of α-Cumyl α-Ketoesters via Intermolecular C-H Bond Activation
复制标题
α-枯基 α-酮酯通过分子间 C-H 键活化的光化学和无添加剂偶联反应
DOI：
10.1055/s-0035-1561098
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发表时间：
2016
期刊：
影响因子：
2
通讯作者：
Mikiko Sodeoka
中科院分区：
文献类型：
--
作者：
Eisuke Ota;Yu Mikame;Go Hirai;Shigeru Nishiyama;Mikiko Sodeoka
我们开发了α-酮酯与几种简单醇、烷烃、醚和酰胺的光化学偶联反应。叔烷基酯，α-cumyl酯的使用是避免已知光降解过程的关键。在不添加任何添加剂的LED灯（365 nm）照射下，促进了分子间C-H键的活化和随后的C-C键形成。在偶联体中，与空间要求较低的酰胺的反应可以有效地得到独特的烯酰-β-氨基-α-羟基酸衍生物。以苯或丙酮为溶剂，与固体氨基酸衍生物反应得到四氢-1,4-二氮卓-2,5-二酮衍生物的前体。
We developed a photo-chemical coupling reaction of α-keto esters with several simple alcohols, alkanes, ethers, and amides. Use of tertiary alkyl ester, α-cumyl ester, is the key for avoiding the known photo-degradation process. Intermolecular C–H bond activation and subsequent C–C bond formation were promoted by irradiation with an LED lamp (365 nm) without any additives. Among the coupling partners, reactions with sterically less demanding amides proceeded efficiently to provide uniqueN-acyl-β-amino-α-hydroxy acid derivatives. In benzene or acetone as a solvent, the reaction with a solid amino acid derivative provided a precursor of tetrahydro-1,4-diazepine-2,5-dione derivatives.