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Fluoroalkyl‐Substituted Diazomethanes and Their Application in a General Synthesis of Pyrazoles and Pyrazolines
Author(s) -
Mertens Lucas,
Hock Katharina J.,
Koenigs Rene M.
Publication year - 2016
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.201601707
Subject(s) - microreactor , cycloaddition , acetic acid , catalysis , chemistry , nitrite , combinatorial chemistry , continuous flow , organic chemistry , nitrate , physics , mechanics
A novel continuous‐flow approach for the synthesis of fluoroalkyl‐substituted diazomethanes has been developed. Utilizing a cheap, self‐made microreactor fluoroalkyl‐substituted amines were transformed into the corresponding diazomethanes using tert ‐butyl nitrite and acetic acid as catalyst. These diazomethanes were employed in [2+3] cycloaddition reactions with olefins and alkynes, yielding valuable pyrazolines and pyrazoles in good to excellent yields.