Mechanistic Insights on Azide-Nitrile Cycloadditions: On the Dialkyltin Oxide-Trimethylsilyl Azide Route and a New Vilsmeier-Haack-Type Organocatalyst
David Cantillo, Bernhard Gutmann and C. Oliver Kappe*
*Christian Doppler Laboratory for Microwave Chemistry (CDLMC)
and Institute of Chemistry, Karl-Franzens-University Graz, Heinrichstrasse 28,
A-8010 Graz, Austria, Email: oliver.kappe
uni-graz.at
D. Cantillo, B. Gutmann, C. O. Kappe, J. Am. Chem. Soc., 2011, 133, 4465-4475.
DOI: 10.1021/ja109700b
Abstract
An organocatalyst, 5-azido-1-methyl-3,4-dihydro-2H-pyrrolium azide, generated in situ from N-methyl-2-pyrrolidone (NMP), sodium azide, and trimethylsilyl chloride, enables the formation of tetrazoles by cycloaddition of sodium azide with organic nitriles under neutral conditions and microwave heating. The organocatalyst accelerates the azide-nitrile coupling by activating the nitrile substrate.
see article for more examples
Formation of organocatalyst followed by catalytic cycle
An Experimental and Computational Assessment of Acid-Catalyzed Azide-Nitrile Cycloadditions
D. Cantillo, B. Gutmann, C. O. Kappe, J. Org. Chem., 2012, 77, 10882-10890.
Key Words
Tetrazoles, Microwave Synthesis
ID: J48-Y2011-0820
