Difluorodiazoethane (CF2HCHN2 ): A New Reagent for the Introduction of the Difluoromethyl Group

Chem. Eur. J. 2019, 25 (24), 6053-6063

DOI: 10.1002/chem.201804953

Mykhailiuk P.; Koenigs R.

Difluorodiazoethane (CF2HCHN2) is a small reactive diazoalkane. Its synthesis has been pursued since the 1970s, although only in the past three years have considerable advances been made. Today, difluorodiazoethane is a versatile reagent applied in [3+2]-cycloadditions, esterification, and carbene transfer reactions. Difluorodiazoethane possesses markedly altered reactivity compared to the well-studied trifluorodiazoethane (CF3CHN2). In this article, we discuss the differences between the two reagents: CF2HCHN2 and CF3CHN2. We highlight applications of difluorodiazoethane in organic synthesis, discuss bench-stable analogues, and its unexplored areas.


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