Mechanism of metalated pyrrole-singlet oxygen chemiluminescent reaction

Visible-light-mediated dearomatisation of pyrroles is a powerful strategy for the synthesis of pharmaceuticals and bioactive compounds. Herein we present the chemiluminescent reaction between pyrrole metalated-Ir(III) complex [Ir(K-C,N(2)-DPP)(H)(Cl)(PPh3)(2)] (1) and singlet oxygen to form a ketoamide complex [Ir(K-2 (C,N)-ketoamide)(H)(Cl)(PPh3)(2)] (2). Complex 2 are fully characterized by NMR and single crystal X-ray diffraction analysis. The reaction mechanism of metalated pyrrole-singlet reaction upon irradiation is studied by experiment and DFT calculations.

Automated summary

The visible-light-mediated dearomatisation of pyrroles is a powerful strategy for synthesizing pharmaceuticals and bioactive compounds. In this study, we report a chemiluminescent reaction between a pyrrole metalated-Ir(III) complex and singlet oxygen, resulting in the formation of a ketoamide complex. The reaction mechanism of this metalated pyrrole-singlet oxygen reaction under irradiation is investigated through experiment and DFT calculations.