Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 362, Issue 18, Pages 3872-3885Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202000566
Keywords
manganese catalysis; ketone-amine-alkyne coupling; sustainability; multicomponent reactions; DFT calculations
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Funding
- Hellenic Foundation for Research and Innovation (H.F.R.I.) under the First Call for H. F.R.I. Research Projects to support Faculty members and Researchers and the procurement of high-cost research equipment grant [16-Acronym: SUSTAIN]
- European Funding: Horizon 2020-MSCA [ITN-EJD CATMEC 14/06-721223]
- COST Action (C H Activation in Organic Synthesis -CHAOS) [CA15106]
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Herein, we report a catalytic system based on the earth-abundant manganese for the ketone, amine, alkyne (KA(2)) reaction. The efficiency of manganese manifests at relatively high temperatures, combined with sustainable reaction conditions, and provides a tool for accessing propargylamines from structurally diverse starting materials, including synthetically relevant and bioactive molecules. Our efforts were also aimed at shedding light on the catalytic mode of action of manganese in this transformation, in order to explain its temperature-related behavior. The use of computational methods reveals mechanistic aspects of this reaction indicating important points regarding the reactivity of both manganese and ketones.
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