Abstract
Catalytic guanylation reactions of amines with carbodiimides have received increasing attention because of the atom-economical preparation of guanidines since 2003. To date, more than 40 catalysts including transition metals, main-group metals, and rare-earth metals have been designed and tested for the guanylation reaction to construct acyclic and cyclic guanidines. In this review, we present a mechanistic consideration on catalytic guanylation reactions of amines with carbodiimides for guanidine synthesis to elucidate its development and importance. Four different types of reaction mechanisms have been well categorized: [2 + 2]-cycloaddition/protonation, insertion/protonation, activation of carbodiimide/nucleophilic addition/intramolecular protonation, and protonation/nucleophilic addition/disassociation. It is useful to understand these reaction processes in order to accelerate the rapid development in related areas to meet the growing need for guanidines.
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