An Electrophilic Bromine Redox Catalysis for the Synthesis of Indole Alkaloid Building Blocks by Selective Aliphatic C−H Amination. Issue 48 (7th November 2018)

• Record Type: Journal Article
• Authors: Bergès, Julien; García, Belén; Muñiz, Kilian
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 48(2018)
• Page Start: 15891
• Page End: 15895
• Publication Date: 2018-11-07
• Subjects: bromine catalysis -- C−H bond amination -- homogeneous catalysis -- iodine(III) reagents -- natural products; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201808939
• Languages: English
• ISSNs: 1433-7851

Abstract

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. 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.