NHC–Cu-Catalyzed Protoboration of Monosubstituted Allenes. Ligand-Controlled Site Selectivity, Application to Synthesis and Mechanism

NHC–Cu-Catalyzed Protoboration of Monosubstituted Allenes. Ligand-Controlled Site Selectivity, Application to Synthesis and Mechanism

Two types of NHC–Cu complexes catalyze protoborations of terminal allenes to afford valuable 1,1- or trisubstituted vinylboron species with high site selectivity and stereoselectivity. The scope of the method, application to natural product synthesis, and mechanistic basis for the observed selectivi...

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Veröffentlicht in:Organic letters 2013-03, Vol.15 (6), p.1414-1417
Hauptverfasser: Meng, Fanke, Jung, Byunghyuck, Haeffner, Fredrik, Hoveyda, Amir H
Format: Artikel
Sprache:eng
Schlagworte:
Alkadienes - chemistry
Catalysis
chemical reactions
chemical structure
Copper - chemistry
Heterocyclic Compounds - chemistry
Ligands
Methane - analogs & derivatives
Methane - chemistry
Molecular Structure
organic compounds
Organometallic Compounds - chemistry
Stereoisomerism
stereoselectivity
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Beschreibung
Zusammenfassung:Two types of NHC–Cu complexes catalyze protoborations of terminal allenes to afford valuable 1,1- or trisubstituted vinylboron species with high site selectivity and stereoselectivity. The scope of the method, application to natural product synthesis, and mechanistic basis for the observed selectivity trends are presented.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol4004178