Overclocking Nitronyl Nitroxide Gold Derivatives in Cross‐Coupling Reactions
Igor Zayakin, E.V. Tretyakov, Anna Ya. Akyeva, Mikhail A. Syroeshkin, Julia V. Burykina, Andrey S. Dmitrenok, Аlexander А. Korlyukov, Darina I. Nasyrova, Irina Yu. Bagryanskaya, Dmitri V. Stass, Valentine P. Ananikov
Abstract
Nitronyl nitroxides are functional building blocks in cutting-edge research fields, such as the design of molecular magnets, the development of redox and photoswitchable molecular systems and the creation of redox-active components for organic and hybrid batteries. The key importance of the nitronyl nitroxide function is to translate molecular-level-optimized structures into nano-scale devices and new technologies. In spite of great importance, efficient and versatile synthetic approaches to these compounds still represent a challenge. Particularly, methods for the direct introduction of a nitronyl nitroxide moiety into aromatic systems possess many limitations. Here, we report gold derivatives of nitronyl nitroxide that can enter Pd(0)-catalysed cross-coupling reactions with various aryl bromides, affording the corresponding functionalized nitronyl nitroxides. Based on the high thermal stability and enhanced reactivity in catalytic transformation, a new reagent is suggested for the synthesis of radical systems via a universal cross-coupling approach.