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Synfacts 2010(6): 0637-0637  
DOI: 10.1055/s-0029-1219878
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Cyclophosphoramidates by Intramolecular C-H Amination

Contributor(s): Victor Snieckus, Wei Gan
H. Lu*, J. Tao*, J. E. Jones, L. Wojtas, X. P. Zhang*
University of South Florida, Tampa, USA
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Publication History

Publication Date:
20 May 2010 (online)

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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.