Journal
GREEN CHEMISTRY
Volume 19, Issue 4, Pages 1109-1116Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6gc03096c
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Funding
- National Natural Science Foundation of China [21673077, 21473058, 21273077]
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Mono-phosphines (L1 and L2) and diphosphines (L3 and L4) with typical pi-acceptor character were prepared and applied in Ir(I)-catalyzed N-alkylation of amines with alcohols. It was found that the pi-acceptor character of the applied phosphines is closely correlated to the catalytic efficiency of the [Ir(COD)Cl](2) complex for this green reaction. Compared to PPh3 as the typical sigma-donor (i.e. with poor pi-acceptor character), L1-L4 all resulted in the efficient N-alkylation of aniline to benzyl-aniline. While L1-L4 coordinated to the Ir(I)-catalyst, the consolidated Ir-P linkages due to pi-backdonation could well protect the Ir-catalyst against deactivation, giving rise to the N-alkylation of aniline. On the other hand, the stabilized Ir-catalyst with the involvement of L2 could be recycled successfully for at least 4 runs in the ionic liquid of [MePh3P] Br without the detectable leaching of Ir and P elements in the organic products.
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