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Published on: March 19, 2020
Cobalt dinitrosoalkane complexes in the C-H functionalization of olefins
Jennifer M Schomaker1, W Christopher Boyd, Ian C Stewart
1Department of Chemistry, University of California, Berkeley, California 94720, USA.
Cobalt dinitrosoalkane complexes catalyze alkene C-H functionalization. These complexes enable alkene addition to Michael acceptors, followed by regeneration of the catalyst and release of functionalized alkenes.
Area of Science:
- Organometallic Chemistry
- Catalysis
- Organic Synthesis
Background:
- C-H functionalization is a key transformation in organic chemistry.
- Cobalt complexes offer unique reactivity for catalytic processes.
Purpose of the Study:
- To demonstrate the utility of cobalt dinitrosoalkane complexes in alkene C-H functionalization.
- To develop a catalytic cycle involving cobalt intermediates for alkene modification.
Main Methods:
- Reaction of alkenes with tetramethylcyclopentadienylcobalt dicarbonyl (Me4CpCo(CO)2) and nitric oxide (NO).
- Deprotonation of intermediate cobalt dinitrosoalkane complexes.
- Addition to Michael acceptors.
- Retrocycloaddition reactions to release functionalized alkenes.
Main Results:
- Formation of cobalt dinitrosoalkane complexes.
- Successful deprotonation and addition to Michael acceptors.
- Regeneration of the cobalt catalyst via retrocycloaddition.
- Release of functionalized alkenes.
Conclusions:
- Cobalt dinitrosoalkane complexes are effective catalysts for alkene C-H functionalization.
- A catalytic cycle involving intermediate cobalt species has been established.
- This method provides a novel route to functionalized alkenes.
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