Studies towards auxiliary assisted positional-selective C-H functionalization: A quest for C-C and C-N bond formation
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The thesis is divided into four chapters. The first chapter describes a Cu(II)-catalyzed oxidative coupling of aromatic amides with dialkyl malonates via a tandem C(sp2)–H activation followed by an intramolecular oxidative N–C bond formation for the construction of synthetically valuable isoindolinones and dihydrobenzoindoles structural scaffolds. The second chapter deals with the picolinamide directed Cu(II)-mediated regioselective N-(hetero)arylation of indoles, pyrazoles and pyrrole via dehydrogenative cross-coupling. The third chapter demonstrates a Rh(III)-catalyzed weak-coordination facilitated C4-selective redox-neutral allylation of indoles expending Morita-Baylis-Hillman (MBH) adducts with functional group diversity. The fourth chapter focuses on a Rh(III)-catalyzed switchable reactivity between C4-selective oxidative alkenylation and alkylation of indoles with allylic alcohols depending on the electronic nature of the directing group and the reaction conditions.
Supervisor: Tharmalingam Punniyamurthy