A one-step, one-pot method for the preparation of dihydroacridine bisphosphonates at room temperature by Fc/Fc+-mediated electrochemical synthesis using (RO)3P (R=alkyl) and acridines in good yields at room temperature is proposed. This is the first example of twofold C–P formation via synchronous aromatic C–H phosphorylation. 9,10-Dihydroacridine derivatives are commonly found as privileged structural motifs in OLEDs, bioactive substances, photocatalysts, and various materials for useful applications. However, synthesis of these compounds from starting materials usually involves multiple stages. To date, no examples have been reported of the formation of geminal bisphosphonates on a single carbon atom through the phosphorylation of a C(sp2)–H aromatic fragment. The proposed method is also applicable for xanthene and acridine orange derivatives, but the yields of the bisphosphonates are lower. The products were characterized using X-ray crystallography. Their redox properties were determined through cyclic voltammetry. Paramagnetic compounds formed under oxidation conditions were analyzed using the electron paramagnetic resonance method.
The Front Cover depicts a relaxing spa treatment offered to a strained cyclopropanol client. The sunlight coming through the window symbolizes how visible light is essential for therapy, and photocatalysts (PC) and key intermediates engaged in the strain-release of cyclopropanol are depicted as spa therapists. The bottle of essential oil illustrates the use of DABSO as the essential source of SO2 gas. The PC therapist′s scissors chop off the radical from the dihydropyridine for SO2 capture and subsequent reaction with the acrylamide bed, eventually yielding SVI oxindoles. More information on this photoredox strategy can be found in the Research Article by T. Khan and co-workers (DOI: 10.1002/ejoc.202500726). Bhavik Parve is acknowledged for the graphic.
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