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Synthesis of Cyclophosphoramidates by Intramolecular C-H Amination

Hongdian Lu, J. Tao, Jennifer E. Jones, Łukasz Wojtas, X. P. Zhang

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Abstract

Significance Reported is a synthesis of six- and seven-membered cyclophosphoramidates by ­cobalt(II)-catalyzed intramolecular C-H amination effected by phosphoryl azides. A previously ­reported method for intramolecular amination of carbonyl azides catalyzed by commercially available [Co(TPP)] (TPP: tetraphenylporphyrin) (J. V. Ruppel, R. M. Kamble, X. P. Zhang Org. Lett. 2007 , 9 , 4889) was found to be ineffective for phosphoryl azide substrates. The success of [Co(II)(Por)] A may be the result of hydrogen-bond interaction between P=O and NH which activates the catalysis.

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What this paper is about

Significance Reported is a synthesis of six- and seven-membered cyclophosphoramidates by ­cobalt(II)-catalyzed intramolecular C-H amination effected by phosphoryl azides. A previously ­reported method for intramolecular amination of carbonyl azides catalyzed by commercially available [Co(TPP)] (TPP: tetraphenylporphyrin) (J. V. Ruppel, R. M. Kamble, X. P. Zhang Org. Lett. 2007 , 9 , 4889) was found to be ineffective for phosphoryl azide substrates. The success of [Co(II)(Por)] A may be the result of hydrogen-bond interaction between P=O and NH which activates the catalysis.

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Available abstract

Significance Reported is a synthesis of six- and seven-membered cyclophosphoramidates by ­cobalt(II)-catalyzed intramolecular C-H amination effected by phosphoryl azides. A previously ­reported method for intramolecular amination of carbonyl azides catalyzed by commercially available [Co(TPP)] (TPP: tetraphenylporphyrin) (J. V. Ruppel, R. M. Kamble, X. P. Zhang Org. Lett. 2007 , 9 , 4889) was found to be ineffective for phosphoryl azide substrates. The success of [Co(II)(Por)] A may be the result of hydrogen-bond interaction between P=O and NH which activates the catalysis.

Key concepts: Amination, Intramolecular force, Chemistry, Tetraphenylporphyrin, Catalysis, Azide, Cobalt, Medicinal chemistry

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