An Electrophilic Bromine Redox Catalysis for the Synthesis of Indole Alkaloid Building Blocks by Selective Aliphatic C−H Amination
Dr. Julien Bergès
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
Search for more papers by this authorDr. Belén García
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
Search for more papers by this authorCorresponding Author
Prof. Dr. Kilian Muñiz
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
ICREA, Pg. Lluís Companys 23, 08010 Barcelona, Spain
Search for more papers by this authorDr. Julien Bergès
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
Search for more papers by this authorDr. Belén García
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
Search for more papers by this authorCorresponding Author
Prof. Dr. Kilian Muñiz
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
ICREA, Pg. Lluís Companys 23, 08010 Barcelona, Spain
Search for more papers by this authorGraphical Abstract
New cat. on the block: C−H amination can be conveniently accomplished within a unique Br(−I/I) catalyst system, which opens versatile access to the synthesis of alkaloid building blocks.
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 the synthesis of alkaloid building blocks. This aspect is demonstrated by a new synthetic approach to aspidospermidine. In addition to the development of the catalyst system, the structures of the involved bromine(I) key catalysts were fully elucidated, including by X-ray analyses.
Supporting Information
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