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

dc.contributor.authorCosman, Jenniferen
dc.contributor.supervisorEvans, P. Andrewen
dc.contributor.supervisorSnieckus, Victor A.en
dc.date2015-08-23 18:05:24.335'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
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dc.relation.ispartofseriesCanadian thesesen
dc.rightsQueen's University's Thesis/Dissertation Non-Exclusive License for Deposit to QSpace and Library and Archives Canadaen
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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
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