Advances in Metal-Catalyzed C–H Borylation and Multicomponent Allylic Substitution Reactions

dc.contributor.authorCosman, Jenniferen
dc.contributor.departmentChemistryen
dc.contributor.supervisorEvans, P. Andrewen
dc.contributor.supervisorSnieckus, Victor A.en
dc.date2015-08-23 18:05:24.335
dc.date.accessioned2015-08-27T00:09:27Z
dc.date.issued2015-08-26
dc.degree.grantorQueen's University at Kingstonen
dc.descriptionThesis (Master, Chemistry) -- Queen's University, 2015-08-23 18:05:24.335en
dc.description.abstractChapter one of this thesis describes the iridium-catalyzed ortho-selective C–H borylation reaction of tertiary benzamides. An iridium(I) complex paired with an electron-deficient phosphine ligand allows for efficient C–H activation and borylation using B2pin2. N,N-diethylbenzamides are challenging substrates for the reaction, however a variety of N,N-diisopropylbenzamides are well tolerated, affording the borylated products in generally high yields and good to excellent regioselectivities. This methodology acts as a complementary method to both Directed ortho Metalation (DoM) and a previously developed meta-selective borylation. We have demonstrated the utility of these boron-containing products by further cross-coupling reactions and DoM chemistry. Chapter two of this thesis describes our efforts towards a transition metal-catalyzed 3-component reaction, combining C–H activation and allylic substitution chemistry. Preliminary results were fraught with issues of compatibility of the required conditions for these two powerful reactions, and therefore a metal-catalyzed 3-component reaction using an aryl halide, diene, and nucleophile was explored as an alternative. Results indicate that this reaction is feasible using cyclic amine nucleophiles, generating aminated proucts containing a new stereogenic center. Attempts to use additional nucleophiles, as well as initial efforts to make the reaction proceed in an enantioselective fashion, will be described.en
dc.description.degreeM.Sc.en
dc.description.restricted-thesisThe contents have not yet been published, so should be restricted to prevent competitors getting an unfair advantage on the work described.en
dc.embargo.liftdate2020-08-24
dc.embargo.terms1825en
dc.identifier.urihttp://hdl.handle.net/1974/13534
dc.language.isoengen
dc.relation.ispartofseriesCanadian thesesen
dc.rightsQueen's University's Thesis/Dissertation Non-Exclusive License for Deposit to QSpace and Library and Archives Canadaen
dc.rightsProQuest PhD and Master's Theses International Dissemination Agreementen
dc.rightsIntellectual Property Guidelines at Queen's Universityen
dc.rightsCopying and Preserving Your Thesisen
dc.rightsCreative Commons - Attribution - CC BYen
dc.rightsThis publication is made available by the authority of the copyright owner solely for the purpose of private study and research and may not be copied or reproduced except as permitted by the copyright laws without written authority from the copyright owner.en
dc.subjectmulticomponent reactionsen
dc.subjectC-H activationen
dc.subjectallylic substitutionen
dc.subjectMizoroki-Heck reactionen
dc.subjectiridium-catalyzed C-H borylationen
dc.titleAdvances in Metal-Catalyzed C–H Borylation and Multicomponent Allylic Substitution Reactionsen
dc.typethesisen
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