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dc.contributor.authorBuchwald, Stephen Leffler
dc.contributor.authorCuezva, Alberto Martinez
dc.contributor.authorHicks, Jacqueline D.
dc.contributor.authorHide, Alan M.
dc.date.accessioned2012-08-02T18:47:51Z
dc.date.available2012-08-02T18:47:51Z
dc.date.issued2009-11
dc.date.submitted2009-06
dc.identifier.issn0002-7863
dc.identifier.issn1520-5126
dc.identifier.urihttp://hdl.handle.net/1721.1/71961
dc.description.abstractWe report the efficient N-arylation of acyclic secondary amides and related nucleophiles with aryl nonaflates, triflates, and chlorides. This method allows for easy variation of the aromatic component in tertiary aryl amides. A new biaryl phosphine with P-bound 3,5-(bis)trifluoromethylphenyl groups was found to be uniquely effective for this amidation. The critical aspects of the ligand were explored through synthetic, mechanistic, and computational studies. Systematic variation of the ligand revealed the importance of (1) a methoxy group on the aromatic carbon of the “top ring” ortho to the phosphorus and (2) two highly electron-withdrawing P-bound 3,5-(bis)trifluoromethylphenyl groups. Computational studies suggest the electron-deficient nature of the ligand is important in facilitating amide binding to the LPd(II)(Ph)(X) intermediate.en_US
dc.description.sponsorshipNational Institutes of Health (U.S.) (grant no. GM-58160)en_US
dc.language.isoen_US
dc.publisherAmerican Chemical Society (ACS)en_US
dc.relation.isversionofhttp://dx.doi.org/10.1021/ja9044357en_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.titlePd-Catalyzed N-Arylation of Secondary Acyclic Amides: Catalyst Development, Scope, and Computational Studyen_US
dc.typeArticleen_US
dc.identifier.citationBuchwald, Stephen Leffler, et al. "Pd-Catalyzed N-Arylation of Secondary Acyclic Amides: Catalyst Development, Scope, and Computational Study." Journal of the American Chemical Society 131.46 (2009): 16720-16734.en_US
dc.contributor.departmentMassachusetts Institute of Technology. Department of Chemistryen_US
dc.contributor.approverBuchwald, Stephen L.
dc.contributor.mitauthorBuchwald, Stephen Leffler
dc.contributor.mitauthorCuezva, Alberto Martinez
dc.contributor.mitauthorHicks, Jacqueline D.
dc.contributor.mitauthorHyde, Alan M.
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.orderedauthorsHicks, Jacqueline D.; Hyde, Alan M.; Cuezva, Alberto Martinez; Buchwald, Stephen L.en
dc.identifier.orcidhttps://orcid.org/0000-0003-3875-4775
dspace.mitauthor.errortrue
mit.licensePUBLISHER_POLICYen_US
mit.metadata.statusComplete


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