34.10.5 β-Fluoroamines (Update 2017)

Abstract

This chapter is an update to the earlier Science of Synthesis contribution (Section 34.10) describing methods for the synthesis of β-fluoroamines. This topic has continued to attract signficant attention from the synthetic community, largely due to the medicinal importance of this class of compounds. A wide variety of new methods have been developed, and this review focuses on examples that were published between 2005 and 2015.

Copper-Catalyzed Three-Component Aminofluorination of Alkenes and 1,3-Dienes: Direct Entry to Diverse β-Fluoroalkylamines

“…Traditionally, the synthesis of β-fluorinated amines has typically proceeded with a multiple-step sequence, e.g., through substitution reactions on aziridines, β-amino alcohols, or β-fluoroalcohols with a fluoride or amine nucleophile . Alternatively, direct 1,2-aminofluorination of alkenes offers an ideal strategy allowing rapid access to β-fluorinated amines from readily available starting materials (Figure B). − Extensive efforts have been devoted to alkene aminofluorination in recent years, which elegantly expedite the synthesis of vicinal aminofluorine scaffolds. , However, the known transformations have been limited to the use of a few specially substituted electron-deficient amines for the preparation of β-fluorosulfonamides, − β-fluorocarbamates, − and β-fluorosulfoximines and the use of azides to realize β-fluoroazides .…”