Aromatic C–H bond cleavage by using a Cu(i) ate-complex

Abstract

In situ X-ray absorption spectroscopy (XAS), infrared (IR) and nuclear magnetic resonance (NMR) techniques were used to identify the structures and reactivity of copper-containing active intermediates in the sp² C–H bond cleavage reaction of electron-deficient aromatics. An ate-complex [Cu(O^tBu)₂]Na was found to be able to cleave the C–H bond of benzothiazole (ArH) producing [ArCu^I(O^tBu)]Na with a rate constant of 3.2 × 10⁻² mol⁻¹ L s⁻¹ at −50 °C and with an activation enthalpy of 0.73 kcal mol⁻¹ at room temperature.