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 TolIF₂ in the gem-difluorination of diazo compounds. Computationally, borosilicate, a common constituent of laboratory glassware, was found to spontaneously activate TolIF₂, 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 TolIF₂, which is prepared by a reproducible, multigram-scale synthesis.

A computational and experimental search for mild Lewis-acidic activators for (difluoroiodo)toluene (TolIF₂) has identified borosilicate glass as the most effective activator (to date) in the gem-difluorination of phenyl diazoacetate derivatives.

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