ORA Thesis: "Synthesis and elaboration of heterocycles via palladium-catalyzed C-H functionalization" - uuid:45d028d2-0548-4f22-a110-49aa97ae8dde



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Reference: Maria Gerelle, (2012). Synthesis and elaboration of heterocycles via palladium-catalyzed C-H functionalization. DPhil. University of Oxford.

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Title: Synthesis and elaboration of heterocycles via palladium-catalyzed C-H functionalization


Chapter 1 is a brief literature review of the most recent progress in the area of C-H functionalization via palladium catalysis. This covers the functionalization of electron deficient arenes and heterocycles with alkenyl and alkyl halides both using inter- and intra-molecular reactions. The chapter also contains an overview of recent work from the Willis group.

Chapter 2 presents the functionalization of electron deficient arenes and alkenyl bromides using palladium catalysis, as well as the use of statistical analysis software for optimizing the cross-coupling reaction.

Chapter 3 describes the cross-coupling of substituted benzoxazoles, benzothiazole and benzimidazole with a range of alkenyl iodides using palladium catalysis. The reaction can tolerate both (E) and (Z) disubstituted alkenes and tri-substituted alkenyl iodides, with retention of the double bond geometry.

Chapter 4 details the synthesis of sultams via an intramolecular C-H functionalization using palladium catalysis. The chapter covers the optimization of the starting material synthesis as well as the cross-coupling reaction. We can access the sulfonamides from cyclohexenone and were able to incorporate a large range of substitution patterns (Scheme 3).

Finally, Chapter 5 contains all the experimental details, general considerations and compound data. All the NMR spectra of novel compounds can be found in the appendix.

Digital Origin:Born digital
Type of Award:DPhil
Level of Award:Doctoral
Awarding Institution: University of Oxford
Notes:This thesis is not currently available via ORA.
About The Authors
institutionUniversity of Oxford
facultyMathematical,Physical & Life Sciences Division - Chemistry - Organic Chemistry
researchGroupWillis Group
oxfordCollegeSt Cross College
fundingEngineering and Physical Sciences Research Council
Dr Michael C. Willis More by this contributor
Bibliographic Details
Issue Date: 2012
Copyright Date: 2012
Urn: uuid:45d028d2-0548-4f22-a110-49aa97ae8dde
Item Description
Member of collection : ora:thesis
Alternate metadata formats
Copyright Holder: Maria Gerelle
Access Condition: Restricted: Full content available from 2015-09-28 (ISO 8601)
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