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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Raoufmoghaddam, Saeed Drent, Eite Bouwman, Elisabeth |
| Description | Author Affiliation: Raoufmoghaddam S ( Leiden Institute of Chemistry, Gorlaeus Laboratories, Leiden University, P.O. Box 9502, 2300 RA Leiden (The Netherlands), Fax: (+31) 71-5274761.) |
| Abstract | A rhodium/xantphos homogeneous catalyst system has been developed for direct chemo- and regioselective mono-N-alkylation of primary amides with 1-alkenes and syngas through catalytic hydroamidomethylation with 1-pentene and acetamide as model substrates. For appropriate catalyst performance, it appears to be essential that catalytic amounts of a strong acid promoter, such as p-toluenesulfonic acid (HOTs), as well as larger amounts of a weakly acidic protic promoter, particularly hexafluoroisopropyl alcohol (HOR(F) ) are applied. Apart from the product N-1-hexylacetamide, the isomeric unsaturated intermediates, hexanol and higher mass byproducts, as well as the corresponding isomeric branched products, can be formed. Under optimized conditions, almost full alkene conversion can be achieved with more than 80% selectivity to the product N-1-hexylamide. Interestingly, in the presence of a relatively high concentration of HOR(F) , the same catalyst system shows a remarkably high selectivity for the formation of hexanol from 1-pentene with syngas, thus presenting a unique example of a selective rhodium-catalyzed hydroformylation-hydrogenation tandem reaction under mild conditions. Time-dependent product formation during hydroamidomethylation batch experiments provides evidence for aldehyde and unsaturated intermediates; this clearly indicates the three-step hydroformylation/condensation/hydrogenation reaction sequence that takes place in hydroamidomethylation. One likely role of the weakly acidic protic promoter, HOR(F) , in combination with the strong acid HOTs, is to establish a dual-functionality rhodium catalyst system comprised of a neutral rhodium(I) hydroformylation catalyst species and a cationic rhodium(III) complex capable of selectively reducing the imide and/or ene-amide intermediates that are in a dynamic, acid-catalyzed condensation equilibrium with the aldehyde and amide in a syngas environment. |
| File Format | HTM / HTML |
| ISSN | 18645631 |
| Issue Number | 9 |
| Volume Number | 6 |
| e-ISSN | 1864564X |
| Journal | ChemSusChem |
| Language | English |
| Publisher | Wiley-VCH |
| Publisher Date | 2013-09-01 |
| Publisher Place | Germany |
| Access Restriction | One Nation One Subscription (ONOS) |
| Subject Keyword | Research Support, Non-u.s. Gov't Alkenes Carbon Monoxide Hydrogen Stereoisomerism Discipline Sustainable Chemistry Substrate Specificity Amides Aldehydes Journal Article Chemistry Rhodium Atmosphere Oxidation-reduction Catalysis Kinetics Methylation |
| Content Type | Text |
| Resource Type | Article |
| Subject | Energy Environmental Chemistry Materials Science Chemical Engineering |
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