Organophotoredox Catalyzed Stereoselective Nitration of Olefins with tert-Butyl Nitrite under Air

An efficient method for the E-selective synthesis of nitroolefins is developed by employing DDQ as the organophotoredox catalyst in combination with tert-BuONO (TBN) as a nitrating agent under visible-light irradiation. This green transition metal-free approach utilizes aerial oxygen as the terminal oxidant and occurs at room temperature. Following the established protocol, 41 different olefines containing broad diversity of substituents were nitrated in good to excellent yields. Mechanistic experiments and photophysical studies revealed the probable mechanism.