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Mechanistic Investi...
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Kleimark, Jonatan,1982Gothenburg University,Göteborgs universitet,Institutionen för kemi,Department of Chemistry
(författare)
Mechanistic Investigation of Iron-Catalyzed Coupling Reactions
- Artikel/kapitelEngelska2009
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LIBRIS-ID:oai:gup.ub.gu.se/95948
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https://gup.ub.gu.se/publication/95948URI
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https://doi.org/10.1002/cctc.200900061DOI
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The mechanism of the iron-catalyzed cross-coupling of aryl electrophiles with alkyl Grignard reagents is studied by a combination of GC monitoring, Hammett competition experiments, and DFT calculations. The reaction follows a pathway where an FeI complex, formed in situ, reacts in a rate-limiting oxidative addition with the aryl electrophile. A rapid thermoneutral transmetalation from a Grignard reagent occurs either before or after the oxidative addition, with little to differentiate between the two pathways. A reductive elimination of the resulting alkyl aryl FeIII complex closes the catalytic cycle. Iron in lower oxidation states can act as a competent precatalyst by oxidation into the FeI-FeIII cycle. FeII complexes can give FeI catalysts through reductive elimination of a bimetallic complex. Added ligands, dilution, and powerful aryl electrophiles all serve to increase the stability of the active catalyst, presumably by counteracting oligomerization of low-valent iron.
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Hedström, Anna,1983Gothenburg University,Göteborgs universitet,Institutionen för kemi,Department of Chemistry(Swepub:gu)xhannh
(författare)
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Larsson, Per-Fredrik,1983Gothenburg University,Göteborgs universitet,Institutionen för kemi,Department of Chemistry(Swepub:gu)xlperm
(författare)
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Johansson, Charlotte,1976Gothenburg University,Göteborgs universitet,Institutionen för kemi,Department of Chemistry(Swepub:gu)xjcham
(författare)
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Norrby, Per-Ola,1962Gothenburg University,Göteborgs universitet,Institutionen för kemi,Department of Chemistry(Swepub:gu)xnorrp
(författare)
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Göteborgs universitetInstitutionen för kemi
(creator_code:org_t)
Sammanhörande titlar
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Ingår i:ChemCatChem: Wiley1:1, s. 152-1611867-38801867-3899
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