Overclocking Nitronyl Nitroxide Gold Derivatives in Cross-Coupling Reactions.

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.