Catalyst-free transfer hydrogenation of activated alkenes exploiting isopropanol as the sole and traceless reductant
Catalyst-free transfer hydrogenation of activated alkenes exploiting isopropanol as the sole and traceless reductant
复制标题
DOI：
10.1039/d2gc04315g
复制
发表时间：
2023-01-04
期刊：
影响因子：
9.8
通讯作者：
Kurti，Laszlo
中科院分区：
文献类型：
--
作者：
Das，Tamal Kanti;Trevino，Agustin M. Rodriguez;Kurti，Laszlo
金属催化和有机催化的转移加氢反应被广泛用于还原CO和CN键。然而，CC键的选择性转移加氢反应仍然具有挑战性。因此，在温和的条件下，在没有金属催化剂的情况下，使用容易获得和廉价的还原剂（即伯醇和仲醇）进行烯烃的化学选择性转移加氢，将标志着绿色转移加氢策略的发展取得重大进展。本文描述了一种以异丙醇为环保还原剂和溶剂的非常规活性烯烃无催化剂转移加氢反应。该反应提供了方便的合成途径，广泛的取代丙二酸半氧酯（SMAHOs）在中等到良好的产率。机械研究指向一个前所未有的氢键辅助转移氢化过程。
Both metal-catalyzed and organocatalytic transfer hydrogenation reactions are widely employed for the reduction of CO and CN bonds. However, selective transfer hydrogenation reactions of CC bonds remain challenging. Therefore, the chemoselective transfer hydrogenation of olefins under mild conditions and in the absence of metal catalysts, using readily available and inexpensive reducing agents (i.e. primary and secondary alcohols), will mark a significant advancement towards the development of green transfer hydrogenation strategies. Described herein is an unconventional catalyst-free transfer hydrogenation reaction of activated alkenes using isopropanol as an eco-friendly reductant and solvent. The reaction gives convenient synthetic access to a wide range of substituted malonic acid half oxyesters (SMAHOs) in moderate to good yields. Mechanistic investigations point towards an unprecedented hydrogen bond-assisted transfer hydrogenation process.