Cobalt-Catalyzed Allylation of Heterobicyclic Alkenes: Ligand-Induced Divergent Reactivities

The allylation of heterobicyclic alkenes is presented for the first time. By using an inexpensive cobalt salt as the catalyst and easy‐to‐handle potassium allyltrifluoroborate as the reagent, an unprecedented formal hydroallylation of the bicyclic alkenes is realized in high efficiency. When a chira...

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Bibliographic Details
Published in:Angewandte Chemie 2015-11, Vol.127 (46), p.13900-13904
Main Authors: Huang, Yuan, Ma, Chao, Lee, Yi Xin, Huang, Rui-Zhi, Zhao, Yu
Format: Article
Language:eng ; ger
Subjects:
Alkene
Alkenes
Allyl compounds
Allylverbindungen
Catalysts
Chemical reactions
Chemistry
Cobalt
P-Liganden
Potassium
Synthesemethoden
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Summary:The allylation of heterobicyclic alkenes is presented for the first time. By using an inexpensive cobalt salt as the catalyst and easy‐to‐handle potassium allyltrifluoroborate as the reagent, an unprecedented formal hydroallylation of the bicyclic alkenes is realized in high efficiency. When a chiral cobalt/bis(phosphine) complex is used instead, the alternative ring‐opening products can be obtained in high yield and excellent enantioselectivity. Phos und Co.: In der Titelreaktion werden ein preiswertes Cobaltsalz als Katalysator und Kaliumallyltrifluoroborat als Reagens verwendet, um eine ungewöhnliche formale Hydroallylierung von bicyclischen Alkenen durchzuführen. Wird stattdessen ein chiraler Cobalt‐Bisphosphan‐Komplex eingesetzt, erhält man die ringgeöffneten Produkte in hoher Ausbeute mit exzellenter Enantioselektivität. TBAI=Tetra‐n‐butylammoniumiodid.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201506003