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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Hoi, Ka Hou Froese, Robert D. J. Hopkinson, Alan C. Organ, Michael G. Çalimsiz, Selçuk |
| Description | Author Affiliation: Hoi KH ( Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3, Canada.) |
| Abstract | The amination of aryl chlorides with various aniline derivatives using the N-heterocyclic carbene-based Pd complexes Pd-PEPPSI-IPr and Pd-PEPPSI-IPent (PEPPSI=pyridine, enhanced precatalyst, preparation, stabilization, and initiation; IPr=diisopropylphenylimidazolium derivative; IPent= diisopentylphenylimidazolium derivative) has been studied. Rate studies have shown a reliance on the aryl chloride to be electron poor, although oxidative addition is not rate limiting. Anilines couple best when they are electron rich, which would seem to discount deprotonation of the intermediate metal ammonium complex as being rate limiting in favour of reductive elimination. In previous studies with secondary amines using PEPPSI complexes, deprotonation was proposed to be the slow step in the cycle. These experimental findings relating to mechanism were corroborated by computation. Pd-PEPPSI-IPr and the more hindered Pd-PEPPSI-IPent catalysts were used to couple deactivated aryl chlorides with electron poor anilines; while the IPr catalysis was sluggish, the IPent catalyst performed extremely well, again showing the high reactivity of this broadly useful catalyst. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 1 |
| Volume Number | 18 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2012-01-02 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Chemistry |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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