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DOI: 10.1055/s-0040-1707271
Redox-Neutral Propargylic C–H Functionalization by Using Iron Catalysis
We thank the University of Pittsburgh for generous startup support.
Abstract
In spite of their rich stoichiometric chemistry, cyclopentadienyliron(II) dicarbonyl complexes are rarely used as catalysts in organic synthesis. Inspired by precedents in the chemistry of cationic olefin complexes and neutral allylmetal species, our group has developed a coupling of alkynes or alkenes with aldehydes and other carbonyl electrophiles to give homopropargylic and homoallylic alcohols, respectively, by using a substituted cyclopentadienyliron(II) dicarbonyl complex as the catalyst. In this article, we first contextualize this development within the conceptual background of C–H functionalization chemistry and relative to key stoichiometric precedents. We then give an account of our group’s discovery and development of the catalytic α-functionalization of alkenes and alkynes with electrophilic reagents.
Introduction
Preliminary Stoichiometric Work
Hydroxyalkylation Development and Scope
Conclusions and Future Directions
Key words
C–H functionalization - iron catalysis - homopropargylic alcohols - coupling reaction - propargylation - allylationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707271.
- Supporting Information
Publication History
Received: 23 June 2020
Accepted after revision: 20 July 2020
Article published online:
08 September 2020
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