Site-selective C–H functionalization of pyridines and multi-component reaction of [1.1.1]propellane

Abstract

Pyridine is a significant structural motif commonly found in a range of bio-active compounds, natural products, and pharmaceuticals. Thus, the development of site-selective incorporation of functional groups into pyridines has attracted considerable attention. Especially, various effective methods using pyridinium salts have been developed with high regioselectivity. In addition, [1.1.1]propellane has been identified as the attractive bioisosteres for small ring derivatives in drug design. Due to the unique reactivity of the inverted bond between the two central carbon atoms, it can react with metal catalysts to deliver metal-carbene complexes, which can be used in multi-component reactions. Chapter 1 introduces the site-selective functionalization of pyridines by single electron transfer via the formation of FLP between N-amidopyridinium salts and phosphines. Chapter 2 introduces multi-component reaction of [1.1.1]propellane using silver catalyst and ether solvent. The metal-carbene complexes undergo carbene transfer reaction, providing the exo-methylene cyclobutane derivatives.