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dc.contributor.authorUeda, Satoshi
dc.contributor.authorSu, Mingjuan
dc.contributor.authorBuchwald, Stephen Leffler
dc.date.accessioned2013-11-04T14:13:51Z
dc.date.available2013-11-04T14:13:51Z
dc.date.issued2011-11
dc.date.submitted2011-10
dc.identifier.issn0002-7863
dc.identifier.issn1520-5126
dc.identifier.urihttp://hdl.handle.net/1721.1/81961
dc.description.abstractThe completely N[superscript 1]-selective Pd-catalyzed arylation of unsymmetric imidazoles with aryl halides and triflates is described. This study showed that imidazoles have a strong inhibitory effect on the in situ formation of the catalytically active Pd(0)–ligand complex. The efficacy of the N-arylation reaction was improved drastically by the use of a preactivated solution of Pd[subscript 2](dba)[subscript 3] and L1. From these findings, it is clear that while imidazoles can prevent binding of L1 to Pd, once the ligand is bound to the metal, these heterocycles do not displace it. The utility of the present catalytic system was demonstrated by the regioselective synthesis of the clinically important tyrosine kinase inhibitor nilotinib.en_US
dc.description.sponsorshipNational Institutes of Health (U.S.) (GM58160)en_US
dc.language.isoen_US
dc.publisherAmerican Chemical Society (ACS)en_US
dc.relation.isversionofhttp://dx.doi.org/10.1021/ja2102373en_US
dc.rightsArticle is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.en_US
dc.sourcePMCen_US
dc.titleCompletely N[superscript 1]-Selective Palladium-Catalyzed Arylation of Unsymmetric Imidazoles: Application to the Synthesis of Nilotiniben_US
dc.typeArticleen_US
dc.identifier.citationUeda, Satoshi, Mingjuan Su, and Stephen L. Buchwald. "Completely N1-Selective Palladium-Catalyzed Arylation of Unsymmetric Imidazoles: Application to the Synthesis of Nilotinib.” Journal of the American Chemical Society 134, no. 1 (January 11, 2012): 700-706.en_US
dc.contributor.departmentMassachusetts Institute of Technology. Department of Chemistryen_US
dc.contributor.mitauthorUeda, Satoshien_US
dc.contributor.mitauthorSu, Mingjuanen_US
dc.contributor.mitauthorBuchwald, Stephen Leffleren_US
dc.relation.journalJournal of the American Chemical Societyen_US
dc.eprint.versionAuthor's final manuscripten_US
dc.type.urihttp://purl.org/eprint/type/JournalArticleen_US
eprint.statushttp://purl.org/eprint/status/PeerRevieweden_US
dspace.orderedauthorsUeda, Satoshi; Su, Mingjuan; Buchwald, Stephen L.en_US
dc.identifier.orcidhttps://orcid.org/0000-0003-3875-4775
mit.licensePUBLISHER_POLICYen_US
mit.metadata.statusComplete


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