Base-Free Generation of Organic Electron Donors from Air-Stable Precursors

Guillaume Tintori (1) , Pierre Nabokoff (1) , Ruqaya Buhaibeh (1) , David Bergé-Lefranc (2) , Sébastien Redon (1) , Julie Broggi (1) , Patrice Vanelle (1)

1 ICR - Institut de Chimie Radicalaire
2 IMBE - Institut méditerranéen de biodiversité et d'écologie marine et continentale

Organic electron donors (OEDs) are powerful reducing agents recognized for their potential in the reduction of challenging substrates and in original applications. Nonetheless, their low stability in atmospheric oxygen or over time complicates their manipulation and storage. To overcome these constraints and enhance OED practicality, new air- and moisture-stable aminopyridinium carboxylate and carbonate precursors were synthesized and thermally activated to generate the potent electron donor in situ. Carboxylate adducts proved to be excellent latent OED systems, enabling the facile and efficient reduction of challenging substrates. Their reduction properties were correlated to their structural characteristics by thermogravimetric and spectroscopic analysis.

Keywords: carboxylate adducts; decarboxylation; electron transfer; organic electron donors; reduction

Domains: Chemical Sciences; Chemical Sciences; Organic chemistry

Guillaume Tintori, Pierre Nabokoff, Ruqaya Buhaibeh, David Bergé-Lefranc, Sébastien Redon, et al.. Base-Free Generation of Organic Electron Donors from Air-Stable Precursors. Angewandte Chemie International Edition, 2018, Angewandte Chemie International Edition, 57 (12), pp.3148-3153. ⟨10.1002/anie.201713079⟩. ⟨hal-02079702⟩