Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 28, Issue 57, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202201808
Keywords
2-piperazinone; diamination; oxygen; palladium; piperazine
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Funding
- National Key R&D Program of China [2018YFE0126800]
- Science and Technology Commission of Shanghai Municipality [19JC1430100]
- National Natural Science Foundation of China [21831005]
- Research Foundation of Education Bureau of Hunan Province [19K079]
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In this study, a palladium-catalyzed aerobic oxidation reaction was reported for the synthesis of piperazines and 2-piperazinones using conjugated dienes and ethanediamine, alpha-amino amide derivatives as nitrogen sources, respectively.
Dinitrogen heterocycles are among the most important molecular structures, and the synthesis of these types of structures through intermolecular 1,2-diamination of olefins is a direct and efficient method. However, the types of nitrogen sources are mostly derived from ureas or arylamines, and nitrogen sources from aliphatic amines are still limited due to their distinct electronic and steric effects. Herein, we report a palladium-catalyzed aerobic intermolecular 1,2-diamination of conjugated dienes, using ethanediamine and alpha-amino amide derivatives as nitrogen sources respectively, for the synthesis of piperazines and 2-piperazinones in good yields (up to 95%) and with high regio-and chemoselectivities.
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