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dc.contributor.authorPoh, Jian Siang
dc.date.accessioned2017-11-09T13:14:54Z
dc.date.available2017-11-09T13:14:54Z
dc.date.issued2017-11-08
dc.identifier.urihttps://www.repository.cam.ac.uk/handle/1810/268223
dc.description.abstractIn recent years, the exploitation of flow technologies as an enabling tool to access unique chemical reactivity has flourished. This dissertation describes the utilisation of these flow methods to access new sets of highly versatile, unstable diazo compounds and their application in coupling reactions. In the first chapter, an introduction into the structure and reactivity of diazo compounds is provided, as well as a discussion of currently available methods for their generation. The second chapter describes the coupling of flow-generated, semi-stabilised diazo compounds with terminal alkynes for the synthesis of racemic di- and trisubstituted allenes, using copper(I) catalysis. The third chapter follows with an account of creating chiral disubstituted allenes by asymmetric coupling of flow-generated, semi-stabilised aryl aldehyde-derived diazo compounds with terminal alkynes, using a copper(I) catalyst and a newly developed pyridine(bisimidazoline) ligand. The fourth chapter describes the generation of new, highly reactive non-stabilised diazo compounds and their reaction with arylboronic acids to allow metal-free ‘protodeboronative’ and ‘oxidative’ C(sp2)-C(sp3) cross-couplings. Finally, the fifth chapter describes the experimental procedures relevant for the results described in Chapters 2-4.
dc.description.sponsorshipCambridge Home and EU Scholarship Scheme (CHESS) UCB Biopharma SPRL
dc.language.isoen
dc.rightsAll Rights Reserveden
dc.rights.urihttps://www.rioxx.net/licenses/all-rights-reserved/en
dc.subjectallenes
dc.subjectcopper
dc.subjectdiazo compounds
dc.subjectflow chemistry
dc.subjectcoupling reactions
dc.subjectasymmetric catalysis
dc.subjectphotochemistry
dc.titleCoupling reactions using flow-generated diazo compounds
dc.typeThesis
dc.type.qualificationlevelDoctoral
dc.type.qualificationnameDoctor of Philosophy (PhD)
dc.publisher.institutionUniversity of Cambridge
dc.publisher.departmentChemistry
dc.date.updated2017-11-08T19:45:49Z
dc.identifier.doi10.17863/CAM.14424
dc.contributor.orcidPoh, Jian Siang [0000-0002-6173-8290]
dc.publisher.collegeRobinson
dc.type.qualificationtitlePhD in Organic Chemistry
cam.supervisorLey, Steven Victor
rioxxterms.freetoread.startdate2017-11-08


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