Cobalt-catalysed reductive C-H alkylation of indoles using carboxylic acids and molecular hydrogen
dc.bibliographicCitation.firstPage | 6439 | |
dc.bibliographicCitation.issue | 9 | |
dc.bibliographicCitation.lastPage | 6450 | |
dc.bibliographicCitation.volume | 8 | |
dc.contributor.author | Cabrero-Antonino, Jose R. | |
dc.contributor.author | Adam, Rosa | |
dc.contributor.author | Junge, Kathrin | |
dc.contributor.author | Beller, Matthias | |
dc.date.accessioned | 2023-04-27T06:45:30Z | |
dc.date.available | 2023-04-27T06:45:30Z | |
dc.date.issued | 2017 | |
dc.description.abstract | The direct CH-alkylation of indoles using carboxylic acids is presented for the first time. The catalytic system based on the combination of Co(acac)3 and 1,1,1-tris(diphenylphosphinomethyl)-ethane (Triphos, L1), in the presence of Al(OTf)3 as co-catalyst, is able to perform the reductive alkylation of 2-methyl-1H-indole with a wide range of carboxylic acids. The utility of the protocol was further demonstrated through the C3 alkylation of several substituted indole derivatives using acetic, phenylacetic or diphenylacetic acids. In addition, a careful selection of the reaction conditions allowed to perform the selective C3 alkenylation of some indole derivatives. Moreover, the alkenylation of C2 position of 3-methyl-1H-indole was also possible. Control experiments indicate that the aldehyde, in situ formed from the carboxylic acid hydrogenation, plays a central role in the overall process. This new protocol enables the direct functionalization of indoles with readily available and stable carboxylic acids using a non-precious metal based catalyst and hydrogen as reductant. | eng |
dc.description.version | publishedVersion | eng |
dc.identifier.uri | https://oa.tib.eu/renate/handle/123456789/12087 | |
dc.identifier.uri | http://dx.doi.org/10.34657/11121 | |
dc.language.iso | eng | |
dc.publisher | Cambridge : RSC | |
dc.relation.doi | https://doi.org/10.1039/c7sc02117h | |
dc.relation.essn | 2041-6539 | |
dc.relation.ispartofseries | Chemical Science 8 (2017), Nr. 9 | eng |
dc.relation.issn | 2041-6520 | |
dc.rights.license | CC BY 3.0 Unported | |
dc.rights.uri | https://creativecommons.org/licenses/by/3.0 | |
dc.subject | Alkenylation | eng |
dc.subject | Alkylation | eng |
dc.subject | Carboxylic acids | eng |
dc.subject | Polycyclic aromatic hydrocarbons | eng |
dc.subject | Control experiments | eng |
dc.subject | Functionalizations | eng |
dc.subject | Indole derivatives | eng |
dc.subject | Molecular hydrogen | eng |
dc.subject | Non-precious metals | eng |
dc.subject | Reaction conditions | eng |
dc.subject | Reductive alkylation | eng |
dc.subject | Substituted indoles | eng |
dc.subject | Catalysts | eng |
dc.subject.ddc | 540 | |
dc.title | Cobalt-catalysed reductive C-H alkylation of indoles using carboxylic acids and molecular hydrogen | eng |
dc.type | article | |
dc.type | Text | |
dcterms.bibliographicCitation.journalTitle | Chemical Science | |
tib.accessRights | openAccess | |
wgl.contributor | LIKAT | |
wgl.subject | Chemie | ger |
wgl.type | Zeitschriftenartikel | ger |
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