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Synthesis 2013; 45(7): 952-958
DOI: 10.1055/s-0032-1316862
DOI: 10.1055/s-0032-1316862
paper
Efficient One-Pot Synthesis of Propargylamines from Mannich Bases through a Retro-Mannich-Type Fragmentation
Further Information
Publication History
Received: 16 January 2013
Accepted after revision: 06 February 2013
Publication Date:
27 February 2013 (online)
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.
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For selected examples of retro-Mannich-type reactions, see: