An Electrophilic Bromine Redox Catalysis Manifold for Indole Alkaloid Building Blocks from Selective Aliphatic C-H Amination

Abstract

A new homogeneous bromine(-I/I) redox catalysis is described, which is based on monomeric bromine(I) compounds containing transferable phthalimidato groups. These catalysts enable intermolecular C-H amination reactions at previously unaccessible aliphatic positions and thus enlarge the synthetic potential of direct C- N bond formation including its application in alkaloid building block synthesis. This aspect is demonstrated for a new synthetic approach to aspidospermidine. In addition to the catalysis development, the structures of the involved bromine(I) key catalysts were fully elucidated including X-ray analyses.