Book Description

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 (Scheme 1), as well as the use of statistical analysis software for optimizing the cross-coupling reaction. Scheme 1: Functionalization of electron deficient arenes using palladium catalysis Chapter 3 describes the cross-coupling of substituted benzoxazoles, benzothiazole and benzimidazole with a range of alkenyl iodides using palladium catalysis (Scheme 2). The reaction can tolerate both (E) and (Z) disubstituted alkenes and tri-substituted alkenyl iodides, with retention of the double bond geometry. 1 x =0, S, NMe - 14 examples 25-99% yield i Scheme 2: Cross-coupling using benzoxazoles, benzothiazole and benzimidazole with alkenyl iodides Chapter 4 details the synthesis of sultams via an intramolecular 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 cyc1ohexenone and were able to incorporate a large range of substitution patterns (Scheme 3). Scheme 3: Synthesis ofsultams from cyclohexenone 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. 2.