Development of C N Coupling Using Mechanochemistry: Catalytic Coupling of Arylsulfonamides and Carbodiimides

D Tan, C Mottillo, AD Katsenis… - Angewandte Chemie …, 2014 - Wiley Online Library
D Tan, C Mottillo, AD Katsenis, V Štrukil, T Friščić
Angewandte Chemie International Edition, 2014Wiley Online Library
Reported herein is the mechanochemical synthesis of sulfonyl guanidines, a family of
molecules which are relevant as pharmaceuticals and herbicides, by direct coupling of
sulfonamides and aromatic or aliphatic carbodiimides. Attempts to conduct the coupling in
solution have either failed or given very low conversions, thus demonstrating
mechanochemistry as the necessary component for the discovery of this synthetic strategy.
Abstract
Reported herein is the mechanochemical synthesis of sulfonyl guanidines, a family of molecules which are relevant as pharmaceuticals and herbicides, by direct coupling of sulfonamides and aromatic or aliphatic carbodiimides. Attempts to conduct the coupling in solution have either failed or given very low conversions, thus demonstrating mechanochemistry as the necessary component for the discovery of this synthetic strategy.
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