Borosilicate Activation of (Difluoroiodo)toluene in the gem-Difluorination of Phenyldiazoacetate Derivatives

A combined experimental and computational investigation was conducted to identify a mild and effective Lewis-acidic activator for TolIF(2) in the gem-difluorination of diazo compounds. Computationally, borosilicate, a common constituent of laboratory glassware, was found to spontaneously activate TolIF(2), and an extensive experimental survey confirmed borosilicate as the most effective activator to date. The key to realizing this borosilicate-activated reaction was the use of high purity TolIF(2), which is prepared by a reproducible, multigram-scale synthesis.