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Difluorodiazoethane (CF 2 HCHN 2 ): A New Reagent for the Introduction of the Difluoromethyl Group
Author(s) -
Mykhailiuk Pavel K.,
Koenigs Rene M.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804953
Subject(s) - reagent , carbene , reactivity (psychology) , chemistry , organic synthesis , combinatorial chemistry , group (periodic table) , organic chemistry , medicinal chemistry , catalysis , medicine , alternative medicine , pathology
Difluorodiazoethane (CF 2 HCHN 2 ) 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 (CF 3 CHN 2 ). In this article, we discuss the differences between the two reagents: CF 2 HCHN 2 and CF 3 CHN 2 . We highlight applications of difluorodiazoethane in organic synthesis, discuss bench‐stable analogues, and its unexplored areas.