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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 51, 2021 - Issue 12
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Articles

Synthesis and characterization of new highly fluorinated phosphoramidates

F. Laribia Laboratory of Structural Organic Chemistry: Synthesis and Physico-Chemical Studies, Department of Chemistry, Faculty of Sciences of Tunis, University of Tunis El-Manar, Tunis, Tunisia;b Laboratoire de RMN en Milieu Orienté, Université Paris-Sud 11, ICMMO, UMR CNRS 8182, FranceView further author information
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M. A. K. Sanhourya Laboratory of Structural Organic Chemistry: Synthesis and Physico-Chemical Studies, Department of Chemistry, Faculty of Sciences of Tunis, University of Tunis El-Manar, Tunis, Tunisia;c Materials Chemistry Research Unit, Department of Chemistry, Faculty of Sciences and Techniques, UNA, Nouakchott, MauritaniaCorrespondence[email protected]
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H. Mechia Laboratory of Structural Organic Chemistry: Synthesis and Physico-Chemical Studies, Department of Chemistry, Faculty of Sciences of Tunis, University of Tunis El-Manar, Tunis, TunisiaView further author information
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D. Merletb Laboratoire de RMN en Milieu Orienté, Université Paris-Sud 11, ICMMO, UMR CNRS 8182, FranceView further author information
&
I. Chehidia Laboratory of Structural Organic Chemistry: Synthesis and Physico-Chemical Studies, Department of Chemistry, Faculty of Sciences of Tunis, University of Tunis El-Manar, Tunis, TunisiaView further author information
Pages 1857-1867 | Received 18 Feb 2021, Published online: 11 Apr 2021
 
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Abstract

A one-pot synthesis of new bis(polyfluoroalkyl)dialkylaminophosphoramidates (RF(CH2)2O)2P(O)NR2 (1–6) (RF = C6F13, NR2 = NC5H10 (1), NC4H8 (2), NEt2 (3); RF = C8F17, NR2 = NC5H10 (4), NC4H8 (5), NEt2 (6)) and polyfluoroalkyl bis(dialkylamino)phosphoramidates RF(CH2)2OP(O)(NR2)2 (9–14) (RF = C6F13, NR2 = NC5H10 (9), NC4H8 (10), NEt2 (11); RF = C8F17, NR2 = NC5H10 (12), NC4H8 (13), NEt2 (14)) was performed through phosphorylation of corresponding highly fluorinated alcohols with P(O)Cl3 in dry diethyl ether followed by aminolysis. However, the former phosphoramidates (1–6) and corresponding morpholinyl derivatives 7 and 8 were alternatively prepared in better yields from phosphoramidation reaction of bis(fluoroalkyl)phosphites with amines in the presence of I2 and H2O2 in dichloromethane. All these phosphoramidates were obtained in good yields and characterized by multinuclear (1H, 13C, 31P and 19F) NMR, IR spectroscopy and HRMS.

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Funding

We are grateful to the Tunisian Ministry of High Education and Scientific Research for financial support [LR99ES14] of this research.

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