Copper-catalyzed Z-selective synthesis of acrylamides and polyacrylamides via alkylidene ketenimines

Xuelun Duan, Nan Zheng (), Ming Li, Gongbo Liu, Xinhao Sun, Qiming Wu and Wangze Song ()
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Xuelun Duan: Dalian University of Technology
Nan Zheng: Dalian University of Technology
Ming Li: Dalian University of Technology
Gongbo Liu: Dalian University of Technology
Xinhao Sun: Dalian University of Technology
Qiming Wu: Dalian University of Technology
Wangze Song: Dalian University of Technology

Nature Communications, 2022, vol. 13, issue 1, 1-10

Abstract: Abstract It remains very important to discover and study new fundamental intermediates consisting of carbon and nitrogen as the abundant elements of organic molecules. The unique alkylidene ketenimine could be formed in situ under mild conditions by an unexpected copper-catalyzed three-component reaction of alkyne, azide and water involving a successive cycloaddition, N2 extrusion and carbene-assisted rearrangement. Only Z-α,β-unsaturated amides instead of E-α,β-unsaturated amides or triazoles were acquired from alkylidene ketenimines with excellent selectivities and stereospecificities. In addition, a series of “approximate” alternating copolymers (poly (triazole-alt-Z-acrylamides)) with high Mns and yields were efficiently afforded by multicomponent polymerization through a very simple operation basing on this multicomponent reaction.

Date: 2022
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DOI: 10.1038/s41467-022-32082-w

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