dc.contributor.author | Buchwald, Stephen Leffler | |
dc.contributor.author | Cuezva, Alberto Martinez | |
dc.contributor.author | Hicks, Jacqueline D. | |
dc.contributor.author | Hide, Alan M. | |
dc.date.accessioned | 2012-08-02T18:47:51Z | |
dc.date.available | 2012-08-02T18:47:51Z | |
dc.date.issued | 2009-11 | |
dc.date.submitted | 2009-06 | |
dc.identifier.issn | 0002-7863 | |
dc.identifier.issn | 1520-5126 | |
dc.identifier.uri | http://hdl.handle.net/1721.1/71961 | |
dc.description.abstract | We 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.sponsorship | National Institutes of Health (U.S.) (grant no. GM-58160) | en_US |
dc.language.iso | en_US | |
dc.publisher | American Chemical Society (ACS) | en_US |
dc.relation.isversionof | http://dx.doi.org/10.1021/ja9044357 | en_US |
dc.rights | Article 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.source | PMC | en_US |
dc.title | Pd-Catalyzed N-Arylation of Secondary Acyclic Amides: Catalyst Development, Scope, and Computational Study | en_US |
dc.type | Article | en_US |
dc.identifier.citation | Buchwald, 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.department | Massachusetts Institute of Technology. Department of Chemistry | en_US |
dc.contributor.approver | Buchwald, Stephen L. | |
dc.contributor.mitauthor | Buchwald, Stephen Leffler | |
dc.contributor.mitauthor | Cuezva, Alberto Martinez | |
dc.contributor.mitauthor | Hicks, Jacqueline D. | |
dc.contributor.mitauthor | Hyde, Alan M. | |
dc.relation.journal | Journal of the American Chemical Society | en_US |
dc.eprint.version | Author's final manuscript | en_US |
dc.type.uri | http://purl.org/eprint/type/JournalArticle | en_US |
eprint.status | http://purl.org/eprint/status/PeerReviewed | en_US |
dspace.orderedauthors | Hicks, Jacqueline D.; Hyde, Alan M.; Cuezva, Alberto Martinez; Buchwald, Stephen L. | en |
dc.identifier.orcid | https://orcid.org/0000-0003-3875-4775 | |
dspace.mitauthor.error | true | |
mit.license | PUBLISHER_POLICY | en_US |
mit.metadata.status | Complete | |