Premium
In Situ Generation of Difluoromethyl Diazomethane for [3+2] Cycloadditions with Alkynes
Author(s) -
Mykhailiuk Pavel K.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201501529
Subject(s) - diazomethane , reagent , in situ , chemistry , cycloaddition , catalysis , chloroform , combinatorial chemistry , solvent , explosive material , organic chemistry
Abstract A novel approach to agrochemically important difluoromethyl‐substituted pyrazoles has been developed based on the elusive reagent CF 2 HCHN 2 , which was synthesized (generated in situ) for the first time and employed in [3+2] cycloaddition reactions with alkynes. The reaction is extremely practical as it is a one‐pot process, does not require a catalyst or the isolation of the potentially toxic and explosive gaseous intermediate, and proceeds in a common solvent, namely chloroform, in air. The reaction is also scalable and allows for the preparation of the target pyrazoles on gram scale.