Advances in Metal-Catalyzed C–H Borylation and Multicomponent Allylic Substitution Reactions
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Authors
Cosman, Jennifer
Date
2015-08-26
Type
thesis
Language
eng
Keyword
multicomponent reactions , C-H activation , allylic substitution , Mizoroki-Heck reaction , iridium-catalyzed C-H borylation
Alternative Title
Abstract
Chapter 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.
Description
Thesis (Master, Chemistry) -- Queen's University, 2015-08-23 18:05:24.335
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ProQuest PhD and Master's Theses International Dissemination Agreement
Intellectual Property Guidelines at Queen's University
Copying and Preserving Your Thesis
Creative Commons - Attribution - CC BY
This 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.