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- Publisher Website: 10.1021/ja062856v
- Scopus: eid_2-s2.0-33746071928
- PMID: 16834374
- WOS: WOS:000238972900030
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Article: Intermolecular amidation of unactivated sp2 and sp3 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion
Title | Intermolecular amidation of unactivated sp2 and sp3 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion |
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Authors | |
Issue Date | 2006 |
Publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.html |
Citation | Journal Of The American Chemical Society, 2006, v. 128 n. 28, p. 9048-9049 How to Cite? |
Abstract | This communication describes the Pd(OAc)2-catalyzed intermolecular amidation reactions of unactivated sp2 and sp3 C-H bonds using primary amides and potassium persulfate. The substrates containing a pendent oxime or pyridine group were amidated with excellent chemo- and regioselectivities. It is noteworthy that reactive C-X bonds were well-tolerated and a variety of primary amides can be effective nucleophiles for the Pd-catalyzed C-H amidation reactions. For the reaction of unactivated sp3 C-H bonds, β-amidation of 1° sp3 C-H bonds versus 2° C-H bonds is preferred. The catalytic reaction is initiated by chelation-assisted cyclopalladation involving C-H bond activation. Preliminary mechanistic study suggested that the persulfate oxidation of primary amides should generate reactive nitrene species, which then reacted with the cyclopalladated complex. Copyright © 2006 American Chemical Society. |
Persistent Identifier | http://hdl.handle.net/10722/168029 |
ISSN | 2021 Impact Factor: 16.383 2020 SCImago Journal Rankings: 7.115 |
ISI Accession Number ID | |
References |
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Thu, HY | en_US |
dc.contributor.author | Yu, WY | en_US |
dc.contributor.author | Che, CM | en_US |
dc.date.accessioned | 2012-10-08T03:14:20Z | - |
dc.date.available | 2012-10-08T03:14:20Z | - |
dc.date.issued | 2006 | en_US |
dc.identifier.citation | Journal Of The American Chemical Society, 2006, v. 128 n. 28, p. 9048-9049 | en_US |
dc.identifier.issn | 0002-7863 | en_US |
dc.identifier.uri | http://hdl.handle.net/10722/168029 | - |
dc.description.abstract | This communication describes the Pd(OAc)2-catalyzed intermolecular amidation reactions of unactivated sp2 and sp3 C-H bonds using primary amides and potassium persulfate. The substrates containing a pendent oxime or pyridine group were amidated with excellent chemo- and regioselectivities. It is noteworthy that reactive C-X bonds were well-tolerated and a variety of primary amides can be effective nucleophiles for the Pd-catalyzed C-H amidation reactions. For the reaction of unactivated sp3 C-H bonds, β-amidation of 1° sp3 C-H bonds versus 2° C-H bonds is preferred. The catalytic reaction is initiated by chelation-assisted cyclopalladation involving C-H bond activation. Preliminary mechanistic study suggested that the persulfate oxidation of primary amides should generate reactive nitrene species, which then reacted with the cyclopalladated complex. Copyright © 2006 American Chemical Society. | en_US |
dc.language | eng | en_US |
dc.publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.html | en_US |
dc.relation.ispartof | Journal of the American Chemical Society | en_US |
dc.title | Intermolecular amidation of unactivated sp2 and sp3 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion | en_US |
dc.type | Article | en_US |
dc.identifier.email | Che, CM:cmche@hku.hk | en_US |
dc.identifier.authority | Che, CM=rp00670 | en_US |
dc.description.nature | link_to_subscribed_fulltext | en_US |
dc.identifier.doi | 10.1021/ja062856v | en_US |
dc.identifier.pmid | 16834374 | - |
dc.identifier.scopus | eid_2-s2.0-33746071928 | en_US |
dc.identifier.hkuros | 137334 | - |
dc.relation.references | http://www.scopus.com/mlt/select.url?eid=2-s2.0-33746071928&selection=ref&src=s&origin=recordpage | en_US |
dc.identifier.volume | 128 | en_US |
dc.identifier.issue | 28 | en_US |
dc.identifier.spage | 9048 | en_US |
dc.identifier.epage | 9049 | en_US |
dc.identifier.isi | WOS:000238972900030 | - |
dc.publisher.place | United States | en_US |
dc.identifier.scopusauthorid | Thu, HY=24923933000 | en_US |
dc.identifier.scopusauthorid | Yu, WY=7403913673 | en_US |
dc.identifier.scopusauthorid | Che, CM=7102442791 | en_US |
dc.identifier.issnl | 0002-7863 | - |