Fluoroalkyl‐Substituted Diazomethanes and Their Application in a General Synthesis of Pyrazoles and Pyrazolines. Issue 28 (6th June 2016)

• Record Type: Journal Article
• Authors: Mertens, Lucas; Hock, Katharina J.; Koenigs, Rene M.
• Is Part Of: Chemistry. Volume 22:Issue 28(2016)
• Page Start: 9542
• Page End: 9545
• Publication Date: 2016-06-06
• Subjects: cycloaddition -- diazo compounds -- fluorine -- heterocycles -- microreactors; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201601707
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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. Abstract : Fluoroalkyl‐substituted diazomethanes could be generated from primary amines using a continuous‐flow microreactor. These valuable reagents were applied in the synthesis of fluoroalkyl‐substituted pyrazolines and pyrazoles (see scheme).