Small fluorinated diazoalkanes are known in organic synthesis since 1943, when Gilman and Jones reported on trifluorodiazoethane. Only in recent years this fluorinated diazo compound found its way into the organic synthesis repertoire and represents a versatile reagent that can be used in different transformations for the construction of fluorinated building blocks.<br/>Interestingly, the closely related difluorodiazoethane was first reported only in 2015. Herein, we report on our efforts to the continuous-flow synthesis of this reagent. We highlight subtle differences between trifluorodiazoethane and difluorodiazoethane, which result in different synthetic strategies of these valuable diazoalkanes.<br/>Last we report on applications of these fluorinated diazo compounds in the synthesis of heterocycles and carbocycles.

Difluorodiazoethane: Applications in cycloaddition reactions

253rd National Meeting (2017)

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