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Please use this identifier to cite or link to this item: http://hdl.handle.net/10773/20938
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dc.contributor.authorDhau, Jaspreet S.pt
dc.contributor.authorSingh, Amritpalpt
dc.contributor.authorKasetti, Yoganjaneyulupt
dc.contributor.authorBhatia, Sonampt
dc.contributor.authorBharatam, Parsad V.pt
dc.contributor.authorBrandao, Paulapt
dc.contributor.authorFelix, Vitorpt
dc.contributor.authorSingh, Kamal N.pt
dc.date.accessioned2017-12-07T20:04:45Z-
dc.date.issued2013pt
dc.identifier.issn0040-4020pt
dc.identifier.urihttp://hdl.handle.net/10773/20938-
dc.description.abstractThe BF3-directed lithiation of 3-chloro- and 3-bromopyridine (1a and 1b, espectively) has been investigated. The reactions of 3-chloro- or 3-bromopyridine-BF3 adduct with LDA (1.3/1.1 equiv) followed by quenching with benzaldehyde or iodine exclusively gave the C-2 substituted products. However, when 2.2 equiv of LDA and dimethyl disulfide was used, a C-6 substituted product was obtained. Dilithiation of 1a and 1b has been studied with and without the involvement of BF3 complexation. The role of Li...F(BF3) interactions has been investigated by experimental and DFT calculations. (C) 2013 Elsevier Ltd. All rights reserved.pt
dc.language.isoengpt
dc.publisherPERGAMON-ELSEVIER SCIENCE LTDpt
dc.relationinfo:eu-repo/grantAgreement/FCT/COMPETE/132936/PTpt
dc.rightsrestrictedAccesspor
dc.subjectREGIOSELECTIVE ORTHO-LITHIATIONpt
dc.subjectDENSITY-FUNCTIONAL THEORYpt
dc.subjectHALOGEN-LITHIUM EXCHANGEpt
dc.subjectX-RAY-STRUCTUREpt
dc.subjectC-2 LITHIATIONpt
dc.subjectTMSCH2LI-LIDMAEpt
dc.subjectBROMOPYRIDINESpt
dc.subjectMETALATIONpt
dc.subjectHALOPYRIDINESpt
dc.subjectPYRIDINESpt
dc.titleA study on the BF3 directed lithiation of 3-chloro- and 3-bromopyridinept
dc.typearticlept
dc.peerreviewedyespt
ua.distributioninternationalpt
degois.publication.firstPage10284pt
degois.publication.issue48pt
degois.publication.lastPage10291pt
degois.publication.titleTETRAHEDRONpt
degois.publication.volume69pt
dc.date.embargo10000-01-01-
dc.relation.publisherversion10.1016/j.tet.2013.10.026pt
dc.identifier.doi10.1016/j.tet.2013.10.026pt
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