Autocatalytic Green Synthesis of Imines in Traceless Medium

Author:

Ivanov Roman1ORCID,Ivanova Elizaveta12ORCID,Merkulov Vladislav12ORCID,Zharkov Mikhail1ORCID,Kuchurov Ilya1ORCID,Zlotin Sergei1ORCID

Affiliation:

1. I. N. Nazarov Laboratory of Fine Organic Synthesis N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences 47 Leninsky Prospect 119991 Moscow Russian Federation

2. Mendeleev University of Chemical Technology of Russia 9 Miusskaya sq. Moscow 125047 Russian Federation

Abstract

AbstractFor the first time, condensations of amines with carbonyl compounds have been performed in supercritical carbon dioxide (sc‐CO2). The reactions with aldehydes or active ketones proceed at moderate temperatures (35–55 °C) without use of external catalysts. The process is autocatalytic: it is accelerated by the carbonic acid generated in situ by interaction between the released water and the CO2 medium. The imine products were obtained in high yields in a crystalline form and did not require further purification. The one‐pot transfer hydrogenation and [4+2] cycloaddition reactions performed in the CO2 medium have uncovered attractive prospects for facile green synthesis of more complex and valuable compounds from the generated in situ imine products.

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry

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