Efficient One-Pot Synthesis of Propargylamines from Mannich Bases through a Retro-Mannich-Type Fragmentation

Abstract

An efficient one-pot synthesis of propargylamines is achieved by copper-catalyzed coupling of phenylacetylenes with Mannich bases through a chlorine(1+) or bromine(1+) ion-initiated retro-Mannich-type fragmentation under mild conditions. The Mannich bases are easily prepared from an electron-rich phenol, formaldehyde, and an amine. The protocol provides an appealing alternative for the construction of propargylamines by a simple one-pot procedure.

Key words

copper - catalysis - coupling - Mannich bases - alkynes - amines

• References

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