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Catalyst-Free Phospha-Nucleophilic Substitution of Hydroxylactams by Diarylphosphine Oxide

[ Vol. 5 , Issue. 2 ]

Author(s):

Fei Qi, Fang Fang and Pengfei Li*   Pages 145 - 149 ( 5 )

Abstract:


Background: A nucleophilic substitution between hydroxylactam and diarylphosphine oxide was developed for synthesizing α-aminophosphine oxide.

Methods: Without a catalyst, hydroxylactams reacted with diarylphosphine oxides smoothly to furnish a series of isoindolo-β-carboline-derived phosphine oxide.

Result: Isoindolo-β-carboline-derived phosphine oxides were obtained in 70-99% yields under mild reaction conditions. Notably, only water was a by-product. The mechanism of the atom-economic synthetic process was also discussed.

Conclusion: The synthetic process is simple, efficiency, atom-economic and with great practical worth.

Keywords:

Catalyst-free, hydrophosphonylation, hydroxylactam, N-acylimium ion, nucleophilic substitution, phosphine oxide.

Affiliation:

Department of Chemistry, Southern University of Science and Technology, 1088 Xueyuan Blvd., Nanshan District, Shenzhen, Department of Chemistry, Southern University of Science and Technology, 1088 Xueyuan Blvd., Nanshan District, Shenzhen, Department of Chemistry, Southern University of Science and Technology, 1088 Xueyuan Blvd., Nanshan District, Shenzhen

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