Intramolecular Alkene Hydroamination with Hybrid Catalysts Consisting of a Metal Salt and a Neutral Organic Base

Stegner P, Fischer C, Nguyen DT, Rösch A, Penafiel J, Langer J, Wiesinger M, Harder S (2020)

Publication Type: Journal article

Publication year: 2020

Journal

DOI: 10.1002/ejic.202000671

Abstract

Hybrid catalysts consisting of alkaline earth iodides (AeI2) and the Schwesinger base ^tBuP4 catalyse the intramolecular alkene hydroamination of H2C=CHCH2CR2CH2NH2 [CR2=CPh2, C(CH2)5, CMe2]. Activities decrease along the row: Ca > Sr >> Mg > Ba. Hybrid catalysts consisting of ^tBuP4 and ZnI2, AlI3, FeCI3 or NaI were found to be fully inactive. Also, the hybrid catalyst ^tBuP3/CaI2 was not active which means that the base strength of the non-nucleophilic organic base must be higher than that of ^tBuP3 (pKa BH⁺ = 38.6). Combinations of ^tBuP4 with CaX2 (X = Cl, Br, OiPr, OTf, NTf2) were found to be fully inactive which may in part be explained by poor solubility. The hybrid catalysis method is therefore limited to the combination ^tBuP4/CaI2 but the iodide ligands may be partially or fully replaced by chiral ligands. Chiral modifications of the hybrid catalysts gave in intramolecular alkene hydroamination ee values up to 33 %.

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How to cite

APA:

Stegner, P., Fischer, C., Nguyen, D.T., Rösch, A., Penafiel, J., Langer, J.,... Harder, S. (2020). Intramolecular Alkene Hydroamination with Hybrid Catalysts Consisting of a Metal Salt and a Neutral Organic Base. European Journal of Inorganic Chemistry. https://doi.org/10.1002/ejic.202000671

MLA:

Stegner, Philipp, et al. "Intramolecular Alkene Hydroamination with Hybrid Catalysts Consisting of a Metal Salt and a Neutral Organic Base." European Journal of Inorganic Chemistry (2020).

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