title: Direct aminoalkylation of arenes, heteroarenes, and alkenes via Ni-catalyzed Negishi cross-coupling reactions.
abstract: A room-temperature Ni-catalyzed cross-coupling of aryl, heteroaryl, and alkenyl electrophiles with aminoalkylzinc bromides, readily available from the corresponding aminoalkyl chlorides via Grignard reagents, was developed. The reaction allows a convenient one-step preparation of various aminoalkyl products, including piperidine and tropane derivatives. Such functionalized amine moieties are widely present in various biologically active molecules. Aryl, heteroaryl, and alkenyl iodides, bromides, chlorides and triflates are suitable electrophiles. A short total synthesis of two natural products, (±)-galipinine and (±)-cusparine, is also reported.
authors.affiliation: Department Chemie, Ludwig-Maximilians-University, Butenandtstr. 5-13, Munich, Germany.
authors.forename: Laurin
authors.initials: L
authors.lastname: Melzig
authors.forename: Teresa
authors.initials: T
authors.lastname: Dennenwaldt
authors.forename: Andrey
authors.initials: A
authors.lastname: Gavryushin
authors.forename: Paul
authors.initials: P
authors.lastname: Knochel
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D000478:Alkylation; D002384:Catalysis; D003432:Cross-Linking Reagents / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000475:Alkenes; D003432:Cross-Linking Reagents; D006571:Heterocyclic Compounds; D006846:Hydrocarbons, Halogenated; D007202:Indicators and Reagents; D011804:Quinolines; C452943:galipinine; C452942:cuspareine; D009532:Nickel