Hloušková Zuzana, Klikar Milan, Pytela Oldřich, Almonasy Numan, Růžička Aleš, Jandová Veronika, Bureš Filip
Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice Studentská 573 Pardubice 53210 Czech Republic
Department of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice Studentská 573 Pardubice 53210 Czech Republic.
RSC Adv. 2019 Jul 31;9(41):23797-23809. doi: 10.1039/c9ra04731j. eCollection 2019 Jul 29.
As an extension of the successful dicyanopyrazine photoredox catalysts, a series of X-shaped push-pull molecules with a systematically altered structure were designed and facilely synthesized; their structure-property relationship was elucidated in detail experimental as well as theoretical calculations. Dicyanopyrazines are proven to be powerful photoredox catalysts with a push-pull arrangement that allows facile property tuning by interchanging a particular part of the D-π-A system. Changing the mutual position of the cyano acceptors and the methoxy, methylthio and thienyl donors as well as modifying the linker allowed wide tuning of the fundamental properties of the catalysts. Contrary to the currently available organic photoredox catalysts, we provided a series of catalysts based on a pyrazine heterocyclic scaffold with easy synthesis and further modification, diverse photoredox characteristics and wide application potential across modern photoredox transformations. The photoredox catalytic activities of the target catalysts were examined in a benchmark cross-dehydrogenative coupling and novel and challenging annulation reactions.
作为成功的二氰基吡嗪光氧化还原催化剂的延伸，设计并轻松合成了一系列结构系统改变的X形推拉分子；通过实验和理论计算详细阐明了它们的结构-性质关系。二氰基吡嗪被证明是具有推拉排列的强大光氧化还原催化剂，通过交换D-π-A体系的特定部分可以轻松调节性质。改变氰基受体与甲氧基、甲硫基和噻吩基供体的相互位置以及修饰连接基，可以广泛调节催化剂的基本性质。与目前可用的有机光氧化还原催化剂不同，我们提供了一系列基于吡嗪杂环支架的催化剂，它们易于合成和进一步修饰，具有多样的光氧化还原特性，在现代光氧化还原转化中具有广泛的应用潜力。在基准交叉脱氢偶联以及新颖且具有挑战性的环化反应中考察了目标催化剂的光氧化还原催化活性。
