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7447270 
Journal Article 
Unprecedented cooperative DBU-CuCl2 catalysis for the incorporation of carbon dioxide into homopropargylic amines leading to 6-methylene-1,3-oxazin-2-ones 
Mancuso, R; Ziccarelli, Ida; Pomelli, CS; Cuocci, C; Della Ca', N; Olivieri, D; Carfagna, C; Gabriele, B 
2020 
Yes 
Journal of Catalysis
ISSN: 0021-9517
EISSN: 1090-2694 
Academic Press Inc. 
387 
145-153 
English 
WOS:000542610400015 
We report the first example of cooperative catalysis by DBU and CuCl2, which allows the carboxylation of homopropargylic amines to high value added 6-methylene-1,3-oxazin-2-ones. This reaction also represents the first efficient method for the catalytic incorporation of CO2 into an acyclic substrate to give oxazinones. DFT calculations are in agreement with a mechanism involving: a) deprotonation of the substrate by DBU; b) CO2 capture with formation of a copper carbamate; c) 6-exo-dig cyclization through intramolecular triple bond insertion; and d) protonolysis, with regeneration of DBU and CuCl2 catalysts. The structure of a representative product has been confirmed by XDR analysis. © 2020 Elsevier Inc. 
Carboxylation; Cooperative catalysis; Copper; Cyclization; Oxazinones 
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