New Platforms for Incorporation of Fluorine-Containing Motifs

Identifier:  TDX:4260

Handle: https://hdl.handle.net/20.500.11797/TDX4260

Authors:  Yue, Wenjun

Abstract:
The organic synthesis strategy developed in this PhD thesis provide access to incorporate diverse fluorine-containing motifs into organic backbones via potoredox catalysis, transition metal catalysis and “Super Electron Donor” chemistry. In chapter 2, a swithcable defluorinative sp3 C-H alkylation of secondary amides that rapidly and reliably integrates gem-difluoroalkene motifs into previously untouched sp3 positions has been developed. In chapter 3, a catalytic monofluoroalkylation of terminal and internal olefins has been achieved. Anti-Markovnikov selectivity was noted in á-olefins, whereas chain-walking events enable remote sp3 C-H site fluoroalkylation in internal olefins. In chapter 4, a modular catalytic technique that streamlines the preparation of gem-difluoroalkanes from unactivated sp3 precursors has been described. Enabled by a harmonious interplay between halogen- and hydrogen-atom transfers, this approach introduces a novel avenue to access drug-discovery-relevant difluorinated alkyl bioisosteres. In chapter 5, a de novo alpha-difluoroalkylation of benzyl amines with trifluoromethylarenes has been introduced. This approach stands out for its simplicity, broad applicability encompassing intricate architectures, impressive scalability, and exceptional chemoselectivity.